NADPH
Star0
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- NADPH
- DrugBank Accession Number
- DB02338
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 745.4209
Monoisotopic: 745.091102105 - Chemical Formula
- C21H30N7O17P3
- Synonyms
- Dihydronicotinamide-adenine dinucleotide phosphate
- Reduced nicotinamide adenine dinucleotide phosphate
- TPNH
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UThioredoxin reductase 1, cytoplasmic Not Available Humans UGlucose-6-phosphate 1-dehydrogenase Not Available Leuconostoc mesenteroides UPteridine reductase 1 Not Available Leishmania major UGlucose--fructose oxidoreductase Not Available Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4) UDihydropyrimidine dehydrogenase [NADP(+)] Not Available Humans UAlpha-aminoadipic semialdehyde synthase, mitochondrial Not Available Humans - 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 (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- (5'->5')-dinucleotides
- Sub Class
- Not Available
- Direct Parent
- (5'->5')-dinucleotides
- Alternative Parents
- Purine nucleotide sugars / Purine ribonucleoside diphosphates / Purine ribonucleoside 2',5'-bisphosphates / Nicotinamide nucleotides / Pentose phosphates / Glycosylamines / Organic pyrophosphates / 6-aminopurines / N-substituted nicotinamides / Monosaccharide phosphates show 16 more
- Substituents
- (5'->5')-dinucleotide / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carboximidic acid show 40 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- NADP, NAD(P)H (CHEBI:16474)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 381Q4X082D
- CAS number
- 53-57-6
- InChI Key
- ACFIXJIJDZMPPO-NNYOXOHSSA-N
- InChI
- InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
- IUPAC Name
- {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
- SMILES
- NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C00005
- PubChem Compound
- 5884
- PubChem Substance
- 46508520
- ChemSpider
- 5673
- ChEBI
- 16474
- ChEMBL
- CHEMBL407009
- ZINC
- ZINC000008215411
- PDBe Ligand
- NDP
- Wikipedia
- Nicotinamide_adenine_dinucleotide_phosphate
- PDB Entries
- 1a4i / 1a80 / 1abn / 1ai9 / 1aoe / 1boz / 1bsv / 1bws / 1c3v / 1cyd … show 1071 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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 5.45 mg/mL ALOGPS logP -1.1 ALOGPS logP -6.6 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 0.66 Chemaxon pKa (Strongest Basic) 4.87 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 18 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 364.15 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 153.87 m3·mol-1 Chemaxon Polarizability 63.54 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7428 Blood Brain Barrier + 0.6119 Caco-2 permeable - 0.6999 P-glycoprotein substrate Substrate 0.6338 P-glycoprotein inhibitor I Non-inhibitor 0.7265 P-glycoprotein inhibitor II Non-inhibitor 0.9402 Renal organic cation transporter Non-inhibitor 0.9328 CYP450 2C9 substrate Non-substrate 0.8001 CYP450 2D6 substrate Non-substrate 0.8281 CYP450 3A4 substrate Substrate 0.5091 CYP450 1A2 substrate Non-inhibitor 0.7366 CYP450 2C9 inhibitor Non-inhibitor 0.8533 CYP450 2D6 inhibitor Non-inhibitor 0.8769 CYP450 2C19 inhibitor Non-inhibitor 0.8308 CYP450 3A4 inhibitor Non-inhibitor 0.8797 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8691 Ames test Non AMES toxic 0.8055 Carcinogenicity Non-carcinogens 0.9193 Biodegradation Not ready biodegradable 0.9851 Rat acute toxicity 2.9312 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9526 hERG inhibition (predictor II) Non-inhibitor 0.6188
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002b-0100001900-1b2711d6d8bdf7d586e0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0000000900-eaf38b623ec8e920dab8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0300103900-1df09ac55a720b4260e4 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004l-6300009800-2fed9d1bf5dff20f9557 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-4302942600-bcddda6bc00d31f5e9b9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004r-0901300000-82a3fc0a18ba419ad29c 1H NMR Spectrum 1D NMR Not Applicable 1H NMR Spectrum 1D NMR Not Applicable 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 284.6448369 predictedDarkChem Lite v0.1.0 [M-H]- 219.28114 predictedDeepCCS 1.0 (2019) [M+H]+ 284.7888369 predictedDarkChem Lite v0.1.0 [M+H]+ 221.17656 predictedDeepCCS 1.0 (2019) [M+Na]+ 286.0608369 predictedDarkChem Lite v0.1.0 [M+Na]+ 226.79655 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsThioredoxin reductase 1, cytoplasmic
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Reduces disulfideprotein thioredoxin (Trx) to its dithiol-containing form (PubMed:8577704). Homodimeric flavoprotein involved in the regulation of cellular redox reactions, growth and differentiation. Contains a selenocysteine residue at the C-terminal active site that is essential for catalysis (Probable). Also has reductase activity on hydrogen peroxide (H2O2) (PubMed:10849437)
- Specific Function
- FAD binding
- Gene Name
- TXNRD1
- Uniprot ID
- Q16881
- Uniprot Name
- Thioredoxin reductase 1, cytoplasmic
- Molecular Weight
- 70905.58 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]
2. DetailsGlucose-6-phosphate 1-dehydrogenase
- Kind
- Protein
- Organism
- Leuconostoc mesenteroides
- Pharmacological action
- Unknown
- General Function
- Catalyzes the oxidation of glucose 6-phosphate to 6-phosphogluconolactone. Can utilize either NADP(+) or NAD(+).
- Specific Function
- glucose-6-phosphate dehydrogenase activity
- Gene Name
- zwf
- Uniprot ID
- P11411
- Uniprot Name
- Glucose-6-phosphate 1-dehydrogenase
- Molecular Weight
- 54440.585 Da
References
3. 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
4. DetailsGlucose--fructose oxidoreductase
- Kind
- Protein
- Organism
- Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- glucose-fructose oxidoreductase activity
- Gene Name
- gfo
- Uniprot ID
- Q07982
- Uniprot Name
- Glucose--fructose oxidoreductase
- Molecular Weight
- 47189.15 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Involved in pyrimidine base degradation (PubMed:1512248). Catalyzes the reduction of uracil and thymine (PubMed:1512248). Also involved the degradation of the chemotherapeutic drug 5-fluorouracil (PubMed:1512248)
- Specific Function
- 4 iron, 4 sulfur cluster binding
- Gene Name
- DPYD
- Uniprot ID
- Q12882
- Uniprot Name
- Dihydropyrimidine dehydrogenase [NADP(+)]
- Molecular Weight
- 111400.32 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Bifunctional enzyme that catalyzes the first two steps in lysine degradation
- Specific Function
- histone binding
- Gene Name
- AASS
- Uniprot ID
- Q9UDR5
- Uniprot Name
- Alpha-aminoadipic semialdehyde synthase, mitochondrial
- Molecular Weight
- 102130.895 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]
Drug created at June 13, 2005 13:24 / Updated at June 28, 2022 00:06