Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Flavin-adenine dinucleotide-N5-isobutyl ketone
- DrugBank Accession Number
- DB03531
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Flavin-adenine dinucleotide-N5-isobutyl ketone (DB03531)
- Weight
- Average: 855.6396
Monoisotopic: 855.198999269 - Chemical Formula
- C31H39N9O16P2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UD-amino-acid oxidase 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
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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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleotides
- Sub Class
- Purine ribonucleotides
- Direct Parent
- Purine ribonucleoside diphosphates
- Alternative Parents
- Pentose phosphates / Alkyldiarylamines / Glycosylamines / Pteridines and derivatives / Organic pyrophosphates / Monosaccharide phosphates / Imidazopyrimidines / Monoalkyl phosphates / Hydroxypyrimidines / Imidolactams show 17 more
- Substituents
- 5,6-dihydropyrimidine / Alcohol / Alkyl phosphate / Alkyldiarylamine / Amidine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group show 37 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- NQOFHJRBABCNHU-UYOVOMPXSA-N
- InChI
- InChI=1S/C31H39N9O16P2/c1-12(2)29(47)40-16-6-14(4)13(3)5-15(16)38(27-21(40)28(46)37-31(48)36-27)7-17(41)22(43)18(42)8-53-57(49,50)56-58(51,52)54-9-19-23(44)24(45)30(55-19)39-11-35-20-25(32)33-10-34-26(20)39/h5-6,10-12,17-19,22-24,30,32,41-45H,7-9H2,1-4H3,(H3-,36,37,46,48,49,50,51,52)/t17-,18+,19+,22-,23+,24+,30+/m0/s1
- IUPAC Name
- 9-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4S)-5-[7,8-dimethyl-5-(2-methylpropanoyl)-4-oxido-2-oxo-1H,2H,5H,10H-benzo[g]pteridin-10-yl]-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-6-imino-6H-9lambda5-purin-9-ylium
- SMILES
- CC(C)C(=O)N1C2=C(C=C(C)C(C)=C2)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)[N+]2=CN=C3C2=NC=NC3=N)C2=C1C([O-])=NC(=O)N2
References
- General References
- Not Available
- External Links
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 0.0931 mg/mL ALOGPS logP 0.03 ALOGPS logP -4.5 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 1.8 Chemaxon pKa (Strongest Basic) 3.38 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 19 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 364.68 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 235.75 m3·mol-1 Chemaxon Polarizability 75.92 Å3 Chemaxon Number of Rings 6 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 - 0.9358 Blood Brain Barrier - 0.6615 Caco-2 permeable - 0.6787 P-glycoprotein substrate Substrate 0.6637 P-glycoprotein inhibitor I Non-inhibitor 0.8019 P-glycoprotein inhibitor II Non-inhibitor 0.9348 Renal organic cation transporter Non-inhibitor 0.9646 CYP450 2C9 substrate Non-substrate 0.7952 CYP450 2D6 substrate Non-substrate 0.8138 CYP450 3A4 substrate Substrate 0.5977 CYP450 1A2 substrate Non-inhibitor 0.823 CYP450 2C9 inhibitor Non-inhibitor 0.8547 CYP450 2D6 inhibitor Non-inhibitor 0.8583 CYP450 2C19 inhibitor Non-inhibitor 0.8392 CYP450 3A4 inhibitor Non-inhibitor 0.8347 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8954 Ames test Non AMES toxic 0.7614 Carcinogenicity Non-carcinogens 0.8003 Biodegradation Not ready biodegradable 0.9855 Rat acute toxicity 2.4720 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9557 hERG inhibition (predictor II) Inhibitor 0.5826
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 216.79942 predictedDeepCCS 1.0 (2019) [M+H]+ 218.73238 predictedDeepCCS 1.0 (2019) [M+Na]+ 225.1892 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the oxidative deamination of D-amino acids with broad substrate specificity (PubMed:16616139, PubMed:17088322, PubMed:17303072, PubMed:18544534, PubMed:20368421, PubMed:20567862, PubMed:20603179, PubMed:22203986, PubMed:23219954, PubMed:23391306, PubMed:25030849, PubMed:25701391, PubMed:29274788, PubMed:29326945, PubMed:30938755, PubMed:31799256, PubMed:32730563, PubMed:33484270, PubMed:34041270, PubMed:37558109, PubMed:38035964). Required to catabolize D-amino acids synthesized endogenously, of gastrointestinal bacterial origin or obtained from the diet, and to use these as nutrients (By similarity). Regulates the level of D-amino acid neurotransmitters in the brain, such as D-serine, a co-agonist of N-methyl D-aspartate (NMDA) receptors, and may modulate synaptic transmission (PubMed:17303072). Catalyzes the first step of the racemization of D-DOPA to L-DOPA, for possible use in an alternative dopamine biosynthesis pathway (PubMed:17303072). Also catalyzes the first step of the chiral inversion of N(gamma)-nitro-D-arginine methyl ester (D-NNA) to its L-enantiomer L-NNA that acts as a nitric oxide synthase inhibitor (By similarity). The hydrogen peroxide produced in the reaction provides protection against microbial infection; it contributes to the oxidative killing activity of phagocytic leukocytes and protects against bacterial colonization of the small intestine (By similarity). Enzyme secreted into the lumen of the intestine may not be catalytically active and could instead be proteolytically cleaved into peptides with antimicrobial activity (By similarity). The hydrogen peroxide produced in the reaction may also play a role in promoting cellular senescence in response to DNA damage (PubMed:30659069). Could act as a detoxifying agent which removes D-amino acids accumulated during aging (PubMed:17303072)
- Specific Function
- D-amino-acid oxidase activity
- Gene Name
- DAO
- Uniprot ID
- P14920
- Uniprot Name
- D-amino-acid oxidase
- Molecular Weight
- 39473.75 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 12, 2020 16:52