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Identification
Name10-Propargyl-5,8-Dideazafolic Acid
Accession NumberDB03541  (EXPT00839)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 477.4693
Monoisotopic: 477.164833493
Chemical FormulaC24H23N5O6
InChI KeyLTKHPMDRMUCUEB-IBGZPJMESA-N
InChI
InChI=1S/C24H23N5O6/c1-2-11-29(13-14-3-8-18-17(12-14)22(33)28-24(25)27-18)16-6-4-15(5-7-16)21(32)26-19(23(34)35)9-10-20(30)31/h1,3-8,12,19H,9-11,13H2,(H,26,32)(H,30,31)(H,34,35)(H3,25,27,28,33)/t19-/m0/s1
IUPAC Name
(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino}phenyl)formamido]pentanedioic acid
SMILES
[H][C@@](CCC(O)=O)(NC(=O)C1=CC=C(C=C1)N(CC#C)CC1=CC=C2NC(N)=NC(=O)C2=C1)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Thymidylate synthaseProteinunknownNot AvailableLactobacillus caseiP00469 details
Thymidylate synthaseProteinunknownNot AvailableEscherichia coli (strain K12)P0A884 details
Thymidylate synthaseProteinunknownNot AvailablePneumocystis cariniiP13100 details
Ribosyldihydronicotinamide dehydrogenase [quinone]ProteinunknownNot AvailableHumanP16083 details
Thymidylate synthaseProteinunknownNot AvailableHumanP04818 details
Putative dehydrogenase/reductase SDR family member 4-like 1ProteinunknownNot AvailableHumanP0CG22 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0204 mg/mLALOGPS
logP1.22ALOGPS
logP1.02ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)1.02ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area174.42 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity127.72 m3·mol-1ChemAxon
Polarizability48.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7435
Blood Brain Barrier-0.7739
Caco-2 permeable-0.8286
P-glycoprotein substrateSubstrate0.7069
P-glycoprotein inhibitor INon-inhibitor0.9258
P-glycoprotein inhibitor IINon-inhibitor0.988
Renal organic cation transporterNon-inhibitor0.8386
CYP450 2C9 substrateNon-substrate0.8102
CYP450 2D6 substrateNon-substrate0.7874
CYP450 3A4 substrateNon-substrate0.5543
CYP450 1A2 substrateNon-inhibitor0.8885
CYP450 2C9 inhibitorNon-inhibitor0.887
CYP450 2D6 inhibitorNon-inhibitor0.9281
CYP450 2C19 inhibitorNon-inhibitor0.8511
CYP450 3A4 inhibitorNon-inhibitor0.8964
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9602
Ames testNon AMES toxic0.7139
CarcinogenicityNon-carcinogens0.949
BiodegradationNot ready biodegradable0.9783
Rat acute toxicity2.5900 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9225
hERG inhibition (predictor II)Non-inhibitor0.6978
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Quinazolinamine
  • Diazanaphthalene
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Quinazoline
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Aminopyrimidine
  • Pyrimidone
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Pyrimidine
  • Primary aromatic amine
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Organoheterocyclic compound
  • Acetylide
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Lactobacillus casei
Pharmacological action
unknown
General Function:
Thymidylate synthase activity
Specific Function:
Provides the sole de novo source of dTMP for DNA biosynthesis.
Gene Name:
thyA
Uniprot ID:
P00469
Molecular Weight:
36579.235 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
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Thymidylate synthase activity
Specific Function:
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name:
thyA
Uniprot ID:
P0A884
Molecular Weight:
30479.475 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
Pneumocystis carinii
Pharmacological action
unknown
General Function:
Thymidylate synthase activity
Specific Function:
Not Available
Gene Name:
THYA
Uniprot ID:
P13100
Molecular Weight:
34361.99 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nadph dehydrogenase (quinone) activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular Weight:
25918.4 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
Human
Pharmacological action
unknown
General Function:
Thymidylate synthase activity
Specific Function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular Weight:
35715.65 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
Human
Pharmacological action
unknown
General Function:
Oxidoreductase activity
Specific Function:
Putative oxidoreductase.
Gene Name:
DHRS4L1
Uniprot ID:
P0CG22
Molecular Weight:
30607.35 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23