Basic Info

Common NameNanafrocin(F05651)
2D Structure
FRCD IDF05651
CAS Number52934-83-5
PubChem CID442757
FormulaC16H14O6
IUPAC Name

2-[(1S,3R)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid

InChI Key

ZCJHPTKRISJQTN-JGVFFNPUSA-N

InChI

InChI=1S/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m0/s1

Canonical SMILES

CC1C2=C(CC(O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O

Isomeric SMILES

C[C@H]1C2=C(C[C@@H](O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O

Synonyms
        
            Nanaomycin A
        
            Nanafrocin
        
            Rosanomycin A
        
            Nanafrocine
        
            Nanafrocinum
        
            52934-83-5
        
            Nanomycin A
        
            UNII-8XBV72641V
        
            CHEBI:48202
        
            (1S,3R)-Nanaomycin A
        
Classifies
                

                  
                    Predicted: Fungal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassIsochromanequinones
SubclassBenzoisochromanequinones
Intermediate Tree NodesNot available
Direct ParentBenzoisochromanequinones
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsBenzoisochromanequinone - Naphthopyranone - Naphthopyran - Naphthoquinone - Naphthalene - Aryl ketone - Quinone - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Benzenoid - Pyran - Vinylogous acid - Ketone - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Properties

Property NameProperty Value
Molecular Weight302.282
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Complexity563
Monoisotopic Mass302.079
Exact Mass302.079
XLogP1.3
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7219
Human Intestinal AbsorptionHIA+0.8431
Caco-2 PermeabilityCaco2+0.6655
P-glycoprotein SubstrateSubstrate0.7547
P-glycoprotein InhibitorNon-inhibitor0.8793
Non-inhibitor0.8898
Renal Organic Cation TransporterNon-inhibitor0.8696
Distribution
Subcellular localizationMitochondria0.7881
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7661
CYP450 2D6 SubstrateNon-substrate0.8334
CYP450 3A4 SubstrateNon-substrate0.5054
CYP450 1A2 InhibitorNon-inhibitor0.7005
CYP450 2C9 InhibitorInhibitor0.7546
CYP450 2D6 InhibitorNon-inhibitor0.7884
CYP450 2C19 InhibitorNon-inhibitor0.7369
CYP450 3A4 InhibitorNon-inhibitor0.6057
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5530
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8579
Non-inhibitor0.8679
AMES ToxicityNon AMES toxic0.6476
CarcinogensNon-carcinogens0.9536
Fish ToxicityHigh FHMT0.9456
Tetrahymena Pyriformis ToxicityHigh TPT0.9767
Honey Bee ToxicityHigh HBT0.7159
BiodegradationNot ready biodegradable0.7040
Acute Oral ToxicityI0.4165
Carcinogenicity (Three-class)Danger0.4524

Model Value Unit
Absorption
Aqueous solubility-3.6950LogS
Caco-2 Permeability0.4933LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5183LD50, mol/kg
Fish Toxicity0.1177pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8459pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.03ppm
Cattle,Edible OffalJapan0.03ppm
Cattle,KidneyJapan0.03ppm
Cattle,LiverJapan0.03ppm
Cattle,FatJapan0.03ppm
Cattle,MuscleJapan0.03ppm