D-tartaric acid

Identification

Name
D-tartaric acid
Accession Number
DB01694  (EXPT03007)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (-)-Tartaric acid
  • (2S,3S)-Tartaric acid
  • (S,S)-Tartaric acid
  • (S,S)-Tartrate
  • D-Tartrate
  • D-threaric acid
  • Levotartaric Acid
Categories
Not Available
UNII
JQO211TF1A
CAS number
147-71-7
Weight
Average: 150.0868
Monoisotopic: 150.016437924
Chemical Formula
C4H6O6
InChI Key
FEWJPZIEWOKRBE-XIXRPRMCSA-N
InChI
InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+
IUPAC Name
(2R,3S)-2,3-dihydroxybutanedioic acid
SMILES
O[[email protected]@H]([[email protected]@H](O)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U2,3-diketo-L-gulonate reductaseNot AvailableEscherichia coli (strain K12)
UGalactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1Not AvailableHuman
UTriggering receptor expressed on myeloid cells 1Not AvailableHuman
UProbable ATP-dependent RNA helicase DDX6Not AvailableHuman
UCytochrome P450Not AvailableThermus thermophilus (strain HB27 / ATCC BAA-163 / DSM 7039)
UHypoxia-inducible factor 1-alpha inhibitorNot AvailableHuman
UD-3-phosphoglycerate dehydrogenaseNot AvailableMycobacterium tuberculosis
UAcyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferaseNot AvailableHelicobacter pylori (strain ATCC 700392 / 26695)
UV-type proton ATPase subunit C 1Not AvailableHuman
UdTDP-4-dehydrorhamnose 3,5-epimeraseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UPutative uncharacterized proteinNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
UPhosphonoacetate hydrolaseNot AvailablePseudomonas fluorescens
UPutative uncharacterized proteinNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
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

Eiji Sato, Akira Yanai, "Method for preparing d-tartaric acid." U.S. Patent US3957579, issued February, 1961.

US3957579
General References
Not Available
External Links
KEGG Compound
C00552
PubChem Compound
447315
PubChem Substance
46508249
ChemSpider
394447
BindingDB
50427212
ChEBI
15673
ChEMBL
CHEMBL225983
HET
SRT
Wikipedia
Tartaric_acid
PDB Entries
1n97 / 1rtv / 1xxn / 2c1l / 2dw7 / 2ixi / 2ixj / 2jbm / 2ot9 / 2p3v
show 49 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)172.5 °CPhysProp
water solubility1E+006 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility161.0 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.8ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.21 m3·mol-1ChemAxon
Polarizability11.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.532
Blood Brain Barrier+0.8035
Caco-2 permeable-0.8783
P-glycoprotein substrateNon-substrate0.7685
P-glycoprotein inhibitor INon-inhibitor0.9789
P-glycoprotein inhibitor IINon-inhibitor0.9739
Renal organic cation transporterNon-inhibitor0.9633
CYP450 2C9 substrateNon-substrate0.8684
CYP450 2D6 substrateNon-substrate0.9168
CYP450 3A4 substrateNon-substrate0.7763
CYP450 1A2 substrateNon-inhibitor0.9357
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9544
CYP450 2C19 inhibitorNon-inhibitor0.9695
CYP450 3A4 inhibitorNon-inhibitor0.8884
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9877
Ames testNon AMES toxic0.9289
CarcinogenicityNon-carcinogens0.6841
BiodegradationReady biodegradable0.9397
Rat acute toxicity1.4627 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9914
hERG inhibition (predictor II)Non-inhibitor0.9749
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Sugar acids and derivatives
Alternative Parents
Short-chain hydroxy acids and derivatives / Beta hydroxy acids and derivatives / Monosaccharides / Fatty acids and conjugates / Dicarboxylic acids and derivatives / Alpha hydroxy acids and derivatives / Secondary alcohols / 1,2-diols / Carboxylic acids / Organic oxides
show 2 more
Substituents
Beta-hydroxy acid / Short-chain hydroxy acid / Sugar acid / Monosaccharide / Hydroxy acid / Dicarboxylic acid or derivatives / Alpha-hydroxy acid / Fatty acid / Secondary alcohol / 1,2-diol
show 7 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2,3-dihydroxybutanedioic acid (CHEBI:15673)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-oh group of donors, nad or nadp as acceptor
Specific Function
Catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate.
Gene Name
dlgD
Uniprot ID
P37672
Uniprot Name
2,3-diketo-L-gulonate reductase
Molecular Weight
36572.395 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
Udp-galactose:beta-n-acetylglucosamine beta-1,3-galactosyltransferase activity
Specific Function
Involved in the biosynthesis of L2/HNK-1 carbohydrate epitope on glycoproteins. Can also play a role in glycosaminoglycan biosynthesis. Substrates include asialo-orosomucoid (ASOR), asialo-fetuin, ...
Gene Name
B3GAT1
Uniprot ID
Q9P2W7
Uniprot Name
Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1
Molecular Weight
38255.675 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
Scaffold protein binding
Specific Function
Stimulates neutrophil and monocyte-mediated inflammatory responses. Triggers release of pro-inflammatory chemokines and cytokines, as well as increased surface expression of cell activation markers...
Gene Name
TREM1
Uniprot ID
Q9NP99
Uniprot Name
Triggering receptor expressed on myeloid cells 1
Molecular Weight
26386.385 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
Rna helicase activity
Specific Function
In the process of mRNA degradation, may play a role in mRNA decapping.
Gene Name
DDX6
Uniprot ID
P26196
Uniprot Name
Probable ATP-dependent RNA helicase DDX6
Molecular Weight
54416.42 Da
Kind
Protein
Organism
Thermus thermophilus (strain HB27 / ATCC BAA-163 / DSM 7039)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q746J6
Uniprot Name
Cytochrome P450
Molecular Weight
44255.71 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Hydroxylates HIF-1 alpha at 'Asp-803' in the C-terminal transactivation domain (CAD). Functions as an oxygen sensor and, under normoxic conditions, the hydroxylation prevents interaction of HIF-1 w...
Gene Name
HIF1AN
Uniprot ID
Q9NWT6
Uniprot Name
Hypoxia-inducible factor 1-alpha inhibitor
Molecular Weight
40285.25 Da
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the reversible oxidation of 3-phospho-D-glycerate to 3-phosphonooxypyruvate, the first step of the phosphorylated L-serine biosynthesis pathway. Also catalyzes the reversible oxidation of 2-hydroxyglutarate to 2-oxoglutarate.
Specific Function
Nad binding
Gene Name
serA
Uniprot ID
P9WNX3
Uniprot Name
D-3-phosphoglycerate dehydrogenase
Molecular Weight
54553.635 Da
Kind
Protein
Organism
Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action
Unknown
General Function
Acyl-[acyl-carrier-protein]-udp-n-acetylglucosamine o-acyltransferase activity
Specific Function
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell.
Gene Name
lpxA
Uniprot ID
O25927
Uniprot Name
Acyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferase
Molecular Weight
29855.195 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Subunit of the peripheral V1 complex of vacuolar ATPase. Subunit C is necessary for the assembly of the catalytic sector of the enzyme and is likely to have a specific function in its catalytic act...
Gene Name
ATP6V1C1
Uniprot ID
P21283
Uniprot Name
V-type proton ATPase subunit C 1
Molecular Weight
43941.245 Da
References
  1. 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
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Dtdp-4-dehydrorhamnose 3,5-epimerase activity
Specific Function
Catalyzes the epimerization of the C3' and C5'positions of dTDP-6-deoxy-D-xylo-4-hexulose, forming dTDP-6-deoxy-L-lyxo-4-hexulose.
Gene Name
rmlC
Uniprot ID
Q9HU21
Uniprot Name
dTDP-4-dehydrorhamnose 3,5-epimerase
Molecular Weight
20766.29 Da
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9KVB4
Uniprot Name
Uncharacterized protein
Molecular Weight
14647.545 Da
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Phosphonoacetate hydrolase activity
Specific Function
Specifically hydrolyzes phosphonoacetate. Does not have activity on other organophosphonates or acetates.
Gene Name
phnA
Uniprot ID
Q51782
Uniprot Name
Phosphonoacetate hydrolase
Molecular Weight
44239.04 Da
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Oxidoreductase activity
Gene Name
Not Available
Uniprot ID
A0A0H2URW2
Uniprot Name
Uncharacterized protein
Molecular Weight
27147.305 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:47