Nadph Dihydro-Nicotinamide-Adenine-Dinucleotidephosphate

Identification

Name
Nadph Dihydro-Nicotinamide-Adenine-Dinucleotidephosphate
Accession Number
DB02338  (EXPT02321)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
381Q4X082D
CAS number
Not Available
Weight
Average: 745.4209
Monoisotopic: 745.091102105
Chemical Formula
C21H30N7O17P3
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)[[email protected]@H]1O[[email protected]](COP(O)(=O)OP(O)(=O)OC[[email protected]]2O[[email protected]]([[email protected]](OP(O)(O)=O)[[email protected]@H]2O)N2C=NC3=C2N=CN=C3N)[[email protected]@H](O)[[email protected]]1O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThioredoxin reductase 1, cytoplasmicNot AvailableHuman
UGlucose-6-phosphate 1-dehydrogenaseNot AvailableLeuconostoc mesenteroides
UPteridine reductase 1Not AvailableLeishmania major
UGlucose--fructose oxidoreductaseNot AvailableZymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
UDihydropyrimidine dehydrogenase [NADP(+)]Not AvailableHuman
UAlpha-aminoadipic semialdehyde synthase, mitochondrialNot AvailableHuman
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

General References
Not Available
External Links
KEGG Compound
C00005
PubChem Compound
5884
PubChem Substance
46508520
ChemSpider
5673
ChEBI
16474
ChEMBL
CHEMBL407009
HET
NDP
PDB Entries
1a4i / 1a80 / 1abn / 1ai9 / 1aoe / 1boz / 1bsv / 1bws / 1c3v / 1cyd
show 621 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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.45 mg/mLALOGPS
logP-1.1ALOGPS
logP-7.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.15 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.87 m3·mol-1ChemAxon
Polarizability63.54 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7428
Blood Brain Barrier+0.6119
Caco-2 permeable-0.6999
P-glycoprotein substrateSubstrate0.6338
P-glycoprotein inhibitor INon-inhibitor0.7265
P-glycoprotein inhibitor IINon-inhibitor0.9402
Renal organic cation transporterNon-inhibitor0.9328
CYP450 2C9 substrateNon-substrate0.8001
CYP450 2D6 substrateNon-substrate0.8281
CYP450 3A4 substrateSubstrate0.5091
CYP450 1A2 substrateNon-inhibitor0.7366
CYP450 2C9 inhibitorNon-inhibitor0.8533
CYP450 2D6 inhibitorNon-inhibitor0.8769
CYP450 2C19 inhibitorNon-inhibitor0.8308
CYP450 3A4 inhibitorNon-inhibitor0.8797
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8691
Ames testNon AMES toxic0.8055
CarcinogenicityNon-carcinogens0.9193
BiodegradationNot ready biodegradable0.9851
Rat acute toxicity2.9312 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9526
hERG inhibition (predictor II)Non-inhibitor0.6188
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0921103300-a94dc77e4683c53f1e1c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0901000000-5fcc7bc2ff00254e837a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0920000000-91a94a0d16f7db6907e1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0036-6900111800-7f73a4ecf431645a13cf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-3901000000-b9bf964190caf0afebde
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-057i-6900000000-f6e201cd60ed9314f31a
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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 / Purine nucleotide sugar / Purine ribonucleoside 2',5'-bisphosphate / Purine ribonucleoside bisphosphate / Purine ribonucleoside diphosphate / Nicotinamide-nucleotide / Pentose phosphate / Pentose-5-phosphate / N-glycosyl compound / Glycosyl compound
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
NADP, NAD(P)H (CHEBI:16474)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thioredoxin-disulfide reductase activity
Specific Function
Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enha...
Gene Name
TXNRD1
Uniprot ID
Q16881
Uniprot Name
Thioredoxin reductase 1, cytoplasmic
Molecular Weight
70905.58 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
Leuconostoc mesenteroides
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Catalyzes the oxidation of glucose 6-phosphate to 6-phosphogluconolactone. Can utilize either NADP(+) or NAD(+).
Gene Name
zwf
Uniprot ID
P11411
Uniprot Name
Glucose-6-phosphate 1-dehydrogenase
Molecular Weight
54440.585 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
Leishmania major
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific 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. Con...
Gene Name
PTR1
Uniprot ID
Q01782
Uniprot Name
Pteridine reductase 1
Molecular Weight
30456.315 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
Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
Pharmacological action
Unknown
General Function
Glucose-fructose oxidoreductase activity
Specific Function
Not Available
Gene Name
gfo
Uniprot ID
Q07982
Uniprot Name
Glucose--fructose oxidoreductase
Molecular Weight
47189.15 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
Protein homodimerization activity
Specific Function
Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
Gene Name
DPYD
Uniprot ID
Q12882
Uniprot Name
Dihydropyrimidine dehydrogenase [NADP(+)]
Molecular Weight
111400.32 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
Saccharopine dehydrogenase (nadp+, l-lysine-forming) activity
Specific Function
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-ketoglutarate reductase and saccharopine dehydrogenase activity, respe...
Gene Name
AASS
Uniprot ID
Q9UDR5
Uniprot Name
Alpha-aminoadipic semialdehyde synthase, mitochondrial
Molecular Weight
102130.895 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:56