7,8-dimethylalloxazine

Identification

Name
7,8-dimethylalloxazine
Accession Number
DB04345  (EXPT02065)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 6,7-Dimethylalloxazine
  • 7,8-dimethylbenzo[g]pteridine-2,4(1H,3H)-dione
  • 7,8-dimethylisoalloxazine
  • lumichrome
  • Riboflavin lumichrome
External IDs
NSC-96911
Categories
UNII
99U1UDJ2HM
CAS number
1086-80-2
Weight
Average: 242.2334
Monoisotopic: 242.080375584
Chemical Formula
C12H10N4O2
InChI Key
ZJTJUVIJVLLGSP-UHFFFAOYSA-N
InChI
InChI=1S/C12H10N4O2/c1-5-3-7-8(4-6(5)2)14-10-9(13-7)11(17)16-12(18)15-10/h3-4H,1-2H3,(H2,14,15,16,17,18)
IUPAC Name
7,8-dimethyl-1H,2H,3H,4H-benzo[g]pteridine-2,4-dione
SMILES
CC1=CC2=NC3=C(N=C2C=C1C)C(=O)NC(=O)N3

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFlavin reductase (NADPH)Not AvailableHuman
URiboflavin biosynthesis protein RibFNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
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
C01727
PubChem Compound
5326566
PubChem Substance
46505545
ChemSpider
4483963
ChEBI
37323
HET
LUM
PDB Entries
1he5 / 1s4m / 2cc6 / 2cc7

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
PropertyValueSource
melting point (°C)>300 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0511 mg/mLALOGPS
logP1.18ALOGPS
logP2.73ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.85ChemAxon
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.98 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.19 m3·mol-1ChemAxon
Polarizability24.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.9385
Caco-2 permeable-0.6664
P-glycoprotein substrateSubstrate0.5174
P-glycoprotein inhibitor INon-inhibitor0.8416
P-glycoprotein inhibitor IINon-inhibitor0.9893
Renal organic cation transporterNon-inhibitor0.9219
CYP450 2C9 substrateNon-substrate0.6912
CYP450 2D6 substrateNon-substrate0.839
CYP450 3A4 substrateNon-substrate0.6577
CYP450 1A2 substrateInhibitor0.9136
CYP450 2C9 inhibitorNon-inhibitor0.9606
CYP450 2D6 inhibitorNon-inhibitor0.9716
CYP450 2C19 inhibitorNon-inhibitor0.943
CYP450 3A4 inhibitorNon-inhibitor0.956
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.975
Ames testNon AMES toxic0.6527
CarcinogenicityNon-carcinogens0.9393
BiodegradationNot ready biodegradable0.9001
Rat acute toxicity2.4426 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9596
hERG inhibition (predictor II)Non-inhibitor0.8262
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
GC-MS Spectrum - GC-MSGC-MSsplash10-001r-5900000000-1e37baccc742ae47cb80
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0fe0-4927000000-0ea568b1e8aa60791c9e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f72-1914000000-c5b81d41885f62e10888
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-0900000000-6d4a787c35bdc162a108
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-0900000000-49685e019b9afa0131a8
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00xr-1960000000-52c2b7935c2b9969b017
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-006t-0910000000-4c7ccdec411ac9f28eb8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-006t-0910000000-3a15eb2aac260d80437c

Taxonomy

Description
This compound belongs to the class of organic compounds known as flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Alloxazines and isoalloxazines
Direct Parent
Flavins
Alternative Parents
Quinoxalines / Pyrimidones / Pyrazines / Benzenoids / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Flavin / Diazanaphthalene / Quinoxaline / Pyrimidone / Pyrazine / Pyrimidine / Benzenoid / Vinylogous amide / Heteroaromatic compound / Lactam
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
7,8-dimethylbenzo[g]pteridine-2,4-dione (CHEBI:37323) / a small molecule (CPD-605)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Riboflavin reductase (nadph) activity
Specific Function
Broad specificity oxidoreductase that catalyzes the NADPH-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone)....
Gene Name
BLVRB
Uniprot ID
P30043
Uniprot Name
Flavin reductase (NADPH)
Molecular Weight
22119.215 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
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Riboflavin kinase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9WZW1
Uniprot Name
Riboflavin biosynthesis protein
Molecular Weight
33613.56 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:26