Ingredient Details :5-Hydroxy-4-methoxy-3-methylnaphtho[2,3-c]furan-1(3H)-one


TCMI-ID: TCMI19627


Physicochemical Property
Ingredient Name 5-Hydroxy-4-methoxy-3-methylnaphtho[2,3-c]furan-1(3H)-one
Pubchem CID 71326701
Iupac name 5-hydroxy-4-methoxy-3-methyl-3H-benzo[f][2]benzofuran-1-one
Molecular Formula C14H12O4
Molecular Weight 244.24
Isomeric smiles CC1C2=C(C=C3C=CC=C(C3=C2OC)O)C(=O)O1
InChI InChI=1S/C14H12O4/c1-7-11-9(14(16)18-7)6-8-4-3-5-10(15)12(8)13(11)17-2/h3-7,15H,1-2H3
InChIKey IWUVUCGZHFPCHH-UHFFFAOYSA-N
External Database Links TCMSID: 4923  
Structural Information
nHA(Number of hydrogen bond acceptors) 4
nHD(Number of hydrogen bond donors) 1
nRot(Number of rotatable bonds) 1
nRing(Number of rings) 3
MaxRing(Number of atoms in the biggest ring) 13
nHet(Number of heteroatoms) 4

Stability
nRig(Number of rigid bonds) 16
Flexibility 0.062
Stereo Centers(Number of stereocenters) 1

Solubility
TPSA(Topological polar surface area) 55.76
logS(The logarithm of aqueous solubility value) -3.332
logP(The logarithm of the n-octanol/water distribution coefficient) 2.891
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) 2.208

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.784
Synthetic accessibility score 3.093
Natural Product-likeness score 1.601
Lipinski Rule Accepted
GSK Rule Accepted
Golden Triangle Accepted

Absorption
Caco-2 Permeability -4.782
MDCK Permeability 1.90E-05
Pgp-substrate 0
HIA(human intestinal absorption) 0.005
F20%(20% Oral Bioavailability) 0.002
F30%(30% Oral Bioavailability) 0.003

Distribution
PPB(Plasma protein binding) 95.40%
VD(Volume Distribution) 0.629
BBB Penetration(Blood brain barrier penetration) 0.455
B3 Penetration(Blood brain barrier penetration) Permeable
Fu(The fraction unbound in plasms) 5.44%

Metabolism
CYP1A2 inhibitor 0.957
CYP1A2 substrate 0.928
CYP2C19 inhibitor 0.589
CYP2C19 substrate 0.411
CYP2C9 inhibitor 0.782
CYP2C9 substrate 0.929
CYP2D6 inhibitor 0.469
CYP2D6 substrate 0.407
CYP3A4 inhibitor 0.46
CYP3A4 substrate 0.194

Excretion
CL(The clearance of a drug) 6.917
T1/2 0.637

Toxicology
NonBiodegradable Rule 0
Pfizer Rule Accepted
SR-MMP 0.802

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.646
IGC50 4.033
LC50FM 4.83
LC50DM 5.966

Reproductive Effects
NR-AR(Androgen receptor) 0.006
NR-AR-LBD(Androgen receptor) 0.21
NR-Aromatase 0.707
NR-ER(Estrogen receptor) 0.14
NR-ER-LBD(Estrogen receptor) 0.694

Allergy
Skin Sensitization Rule 2
Skin Sensitization 0.378

Acute Toxicity
Acute Toxicity Rule 1
Rat Oral Acute Toxicity 0.124

Organ Toxicity
hERG Blockers 0.014
H-HT(The human hepatotoxicity) 0.042
DILI(Drug-induced liver injury) 0.58

Primary Irritation
Eye Corrosion 0.004
Eye Irritation 0.869
Respiratory Toxicity 0.357

Mutagenic Effects
AMES Toxicity 0.438

Tumorigenic Effects
Carcinogencity 0.807
SR-ARE(Antioxidant Response Element) 0.729
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.441
SR-p53 0.903

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