3-iodo-beta-lapachone

ID: ALA4448405

PubChem CID: 85910454

Max Phase: Preclinical

Molecular Formula: C15H13IO3

Molecular Weight: 368.17

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)OC2=C(CC1I)C(=O)C(=O)c1ccccc12

Standard InChI:  InChI=1S/C15H13IO3/c1-15(2)11(16)7-10-13(18)12(17)8-5-3-4-6-9(8)14(10)19-15/h3-6,11H,7H2,1-2H3

Standard InChI Key:  OAYAUCMPKAGALG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   17.7182   -7.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3137   -7.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9048   -7.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4934   -4.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4923   -5.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2003   -5.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1985   -4.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9071   -4.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9060   -5.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3331   -4.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6184   -4.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3319   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6168   -5.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6090   -6.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0298   -6.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0393   -5.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0418   -4.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6185   -3.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7323   -7.0539    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  2  0
 12 16  1  0
 13 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  1  0
 10 17  2  0
 11 18  2  0
 15 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4448405

   3-Iodo-3,4-dihydro-2,2-dimethyl-2h-naphtho[1,2-b]pyran-5,6-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 368.17

Molecular Weight (Monoisotopic): 367.9909

AlogP: 3.17

#Rotatable Bonds: ┄

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.40

Np Likeness Score: 1.28

References

1. Reis WJ, Bozzi ÍAO, Ribeiro MF, Halicki PCB, Ferreira LA, Almeida da Silva PE, Ramos DF, de Simone CA, da Silva Júnior EN..  (2019)  Design of hybrid molecules as antimycobacterial compounds: Synthesis of isoniazid-naphthoquinone derivatives and their activity against susceptible and resistant strains of Mycobacterium tuberculosis.,  27  (18): [PMID:31378595] [10.1016/j.bmc.2019.07.045]

2. Gong Q, Hu J, Wang P, Li X, Zhang X..  (2021)  A comprehensive review on β-lapachone: Mechanisms, structural modifications, and therapeutic potentials.,  210  [PMID:33158575] [10.1016/j.ejmech.2020.112962]

3. Patel OPS, Beteck RM, Legoabe LJ..  (2021)  Antimalarial application of quinones: A recent update.,  210  [PMID:33333397] [10.1016/j.ejmech.2020.113084]

Source

Source(1):

• Scientific Literature