L-erythro-7,8-dihydrobiopterin
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Identification
- Generic Name
- L-erythro-7,8-dihydrobiopterin
- DrugBank Accession Number
- DB04400
- Background
7,8-Dihydrobiopterin is an inhibitor of the enzyme dihydroneopterin aldolase (DHNA), which catalyzes the conversion of 7,8-Dihydrobiopterin to 6-hydroxymethyl-7,8-dihydropterin and glycolaldehyde.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 239.2312
Monoisotopic: 239.101839307 - Chemical Formula
- C9H13N5O3
- Synonyms
- Dihydrobiopterin
- L-erythro-q-Dihydrobiopterin
- q-BH2
- Quinonoid dihydrobiopterin
- External IDs
- HBL
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ANitric oxide synthase, inducible inhibitorHumans ATyrosine 3-monooxygenase inhibitorHumans UPhenylalanine-4-hydroxylase Not Available Humans UPteridine reductase 1 Not Available Leishmania major UPterin-4-alpha-carbinolamine dehydratase Not Available Humans UDihydroneopterin aldolase Not Available Staphylococcus aureus - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pteridines and derivatives
- Sub Class
- Pterins and derivatives
- Direct Parent
- Biopterins and derivatives
- Alternative Parents
- Secondary alkylarylamines / Hydroxypyrimidines / Heteroaromatic compounds / Secondary alcohols / Ketimines / 1,2-diols / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 1,2-diol / Alcohol / Amine / Aromatic heteropolycyclic compound / Azacycle / Biopterin / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyrimidine / Imine
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 7,8-dihydrobiopterin (CHEBI:43029)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 6779-87-9
- InChI Key
- FEMXZDUTFRTWPE-DZSWIPIPSA-N
- InChI
- InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m0/s1
- IUPAC Name
- 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one
- SMILES
- C[C@H](O)[C@H](O)C1=NC2=C(NC1)NC(N)=NC2=O
References
- General References
- Not Available
- External Links
- PDB Entries
- 1dcp / 1dmw / 1dr1 / 1dr3 / 1dr4 / 1dr6 / 1e92 / 1jwk / 1lrm / 1ltz … show 17 more
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 1.63 mg/mL ALOGPS logP -1.4 ALOGPS logP -2.3 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 12.98 Chemaxon pKa (Strongest Basic) 3.73 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 132.33 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 68.11 m3·mol-1 Chemaxon Polarizability 23.1 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-01ox-8930000000-836b0568b603906f549d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-a05da7254388814baa53 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0390000000-801b845ce330cf297aac Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00dl-0290000000-87f152717f823d1fec53 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0095-0910000000-56c540bc4715033432a1 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-009j-2900000000-d4a859c295971454cf16 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000f-3900000000-c025f481a2b9df81e665 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 149.57193 predictedDeepCCS 1.0 (2019) [M+H]+ 151.96794 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.13155 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsNitric oxide synthase, inducible
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body (PubMed:7504305, PubMed:7531687, PubMed:7544004, PubMed:7682706). In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2 (By similarity). As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM (PubMed:25417112). Involved in inflammation, enhances the synthesis of pro-inflammatory mediators such as IL6 and IL8 (PubMed:19688109)
- Specific Function
- arginine binding
- Gene Name
- NOS2
- Uniprot ID
- P35228
- Uniprot Name
- Nitric oxide synthase, inducible
- Molecular Weight
- 131116.3 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsTyrosine 3-monooxygenase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the conversion of L-tyrosine to L-dihydroxyphenylalanine (L-Dopa), the rate-limiting step in the biosynthesis of cathecolamines, dopamine, noradrenaline, and adrenaline. Uses tetrahydrobiopterin and molecular oxygen to convert tyrosine to L-Dopa (PubMed:15287903, PubMed:1680128, PubMed:17391063, PubMed:24753243, PubMed:34922205, PubMed:8528210, Ref.18). In addition to tyrosine, is able to catalyze the hydroxylation of phenylalanine and tryptophan with lower specificity (By similarity). Positively regulates the regression of retinal hyaloid vessels during postnatal development (By similarity)
- Specific Function
- amino acid binding
- Gene Name
- TH
- Uniprot ID
- P07101
- Uniprot Name
- Tyrosine 3-monooxygenase
- Molecular Weight
- 58599.545 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsPhenylalanine-4-hydroxylase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the hydroxylation of L-phenylalanine to L-tyrosine
- Specific Function
- iron ion binding
- Gene Name
- PAH
- Uniprot ID
- P00439
- Uniprot Name
- Phenylalanine-4-hydroxylase
- Molecular Weight
- 51861.565 Da
References
4. DetailsPteridine reductase 1
- Kind
- Protein
- Organism
- Leishmania major
- Pharmacological action
- Unknown
- General Function
- Exhibits a NADPH-dependent biopterin reductase activity. Has good activity with folate and significant activity with dihydrofolate and dihydrobiopterin, but not with quinonoid dihydrobiopterin. Confers resistance to methotrexate (MTX).
- Specific Function
- 6,7-dihydropteridine reductase activity
- Gene Name
- PTR1
- Uniprot ID
- Q01782
- Uniprot Name
- Pteridine reductase 1
- Molecular Weight
- 30456.315 Da
References
5. DetailsPterin-4-alpha-carbinolamine dehydratase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Involved in tetrahydrobiopterin biosynthesis (By similarity). Seems to both prevent the formation of 7-pterins and accelerate the formation of quinonoid-BH2. Coactivator for HNF1A-dependent transcription (By similarity). Regulates the dimerization of homeodomain protein HNF1A and enhances its transcriptional activity (By similarity). Also acts as a coactivator for HNF1B-dependent transcription (PubMed:24204001)
- Specific Function
- 4-alpha-hydroxytetrahydrobiopterin dehydratase activity
- Gene Name
- PCBD1
- Uniprot ID
- P61457
- Uniprot Name
- Pterin-4-alpha-carbinolamine dehydratase
- Molecular Weight
- 11999.515 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
6. DetailsDihydroneopterin aldolase
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Unknown
- General Function
- Catalyzes the conversion of 7,8-dihydroneopterin to 6-hydroxymethyl-7,8-dihydropterin. Can also catalyze the epimerization of carbon 2' of dihydroneopterin to dihydromonapterin.
- Specific Function
- dihydroneopterin aldolase activity
- Gene Name
- folB
- Uniprot ID
- P56740
- Uniprot Name
- Dihydroneopterin aldolase
- Molecular Weight
- 13750.58 Da
References
- Deng H, Callender R, Dale GE: A vibrational structure of 7,8-dihydrobiopterin bound to dihydroneopterin aldolase. J Biol Chem. 2000 Sep 29;275(39):30139-43. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22