NAV

Flaviolin

Identification

Generic Name
Flaviolin
DrugBank Accession Number
DB02521
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 206.1516
Monoisotopic: 206.021523302
Chemical Formula
C10H6O5
Synonyms
  • 2,5,7-Trihydroxy-1,4-naphthalenedione
  • 2,5,7-trihydroxynaphthoquinone
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPrenyltransferaseNot AvailableStreptomyces sp. (strain CL190)
UPutative cytochrome P450Not AvailableStreptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
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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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 naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthoquinones
Direct Parent
Naphthoquinones
Alternative Parents
Quinones / Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Polyols / Enols / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homopolycyclic compound / Aryl ketone / Enol / Hydrocarbon derivative / Ketone / Naphthoquinone / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
naphthoquinone (CHEBI:42646)
Affected organisms
Not Available

Chemical Identifiers

UNII
TH7ZC8J7OE
CAS number
479-05-0
InChI Key
RROPNRTUMVVUED-UHFFFAOYSA-N
InChI
InChI=1S/C10H6O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-3,11-12,14H
IUPAC Name
2,5,7-trihydroxy-1,4-dihydronaphthalene-1,4-dione
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C=C(O)C2=O

References

General References
Not Available
KEGG Compound
C18012
PubChem Compound
160478
PubChem Substance
46505645
ChemSpider
14346744
ChEBI
42646
ChEMBL
CHEMBL1232770
PDBe Ligand
FLV
PDB Entries
1t93 / 1zdw / 2d09 / 8qd3

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility2.4 mg/mLALOGPS
logP1.33ALOGPS
logP1.02Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.78Chemaxon
pKa (Strongest Basic)-5.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area94.83 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity52.11 m3·mol-1Chemaxon
Polarizability18.31 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9862
Blood Brain Barrier-0.5381
Caco-2 permeable+0.5653
P-glycoprotein substrateSubstrate0.5294
P-glycoprotein inhibitor INon-inhibitor0.8477
P-glycoprotein inhibitor IINon-inhibitor0.9226
Renal organic cation transporterNon-inhibitor0.9028
CYP450 2C9 substrateNon-substrate0.7921
CYP450 2D6 substrateNon-substrate0.9085
CYP450 3A4 substrateNon-substrate0.632
CYP450 1A2 substrateInhibitor0.7881
CYP450 2C9 inhibitorInhibitor0.8901
CYP450 2D6 inhibitorNon-inhibitor0.8411
CYP450 2C19 inhibitorNon-inhibitor0.6639
CYP450 3A4 inhibitorNon-inhibitor0.6407
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7289
Ames testAMES toxic0.8204
CarcinogenicityNon-carcinogens0.9226
BiodegradationNot ready biodegradable0.8519
Rat acute toxicity2.5615 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9448
hERG inhibition (predictor II)Non-inhibitor0.8899
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01ri-0910000000-3dd44abc29ba3d3edfc4
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9750000000-e30fdde7df39448f8877
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-6e8fc641d802c5b001d4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-8432e555cebb02e862b9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0390000000-0f0de7f593f72ece7875
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0390000000-1d6e8a8a9374ef16c10b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dr-0900000000-b2b9b1c3c5a893d2d6fc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-3900000000-8976c61c20d3a241d9f0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.9372497
predicted
DarkChem Lite v0.1.0
[M-H]-140.35965
predicted
DeepCCS 1.0 (2019)
[M+H]+149.4474497
predicted
DarkChem Lite v0.1.0
[M+H]+142.75523
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.8737497
predicted
DarkChem Lite v0.1.0
[M+Na]+148.66776
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prenyltransferase
Kind
Protein
Organism
Streptomyces sp. (strain CL190)
Pharmacological action
Unknown
General Function
Transferase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q4R2T2
Uniprot Name
Prenyltransferase
Molecular Weight
33743.98 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. [Article]
Details2. Putative cytochrome P450
Kind
Protein
Organism
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function
Catalyze oxidative C-C coupling reaction to polymerize flaviolin and form highly conjugated pigments which protect the soil bacterium from deleterious effects of UV irradiation (three isomers of bi...
Gene Name
cyp158a2
Uniprot ID
Q9FCA6
Uniprot Name
Biflaviolin synthase CYP158A2
Molecular Weight
44354.085 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:18