3-(((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione

ID: ALA4594201

PubChem CID: 155569589

Max Phase: Preclinical

Molecular Formula: C29H30O8

Molecular Weight: 506.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)O[C@H]2O[C@H](COC3C4=C(OC3(C)C)c3ccccc3C(=O)C4=O)[C@@H](OCc3ccccc3)[C@H]2O1

Standard InChI:  InChI=1S/C29H30O8/c1-28(2)26(20-22(31)21(30)17-12-8-9-13-18(17)23(20)35-28)33-15-19-24(32-14-16-10-6-5-7-11-16)25-27(34-19)37-29(3,4)36-25/h5-13,19,24-27H,14-15H2,1-4H3/t19-,24-,25-,26?,27-/m1/s1

Standard InChI Key:  LIRLLGKTZVCTNS-XTNHUWDISA-N

Molfile:  

 
     RDKit          2D

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   29.2446   -4.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5380   -3.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5358   -4.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4338   -1.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4353   -2.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1430   -2.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1389   -1.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.5589   -0.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9847   -1.1998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2727   -2.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.7296   -3.6378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8755   -2.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6813   -2.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2205   -3.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.3549   -2.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1687   -2.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3365   -3.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1491   -3.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8777   -2.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5390   -4.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   29.9556   -6.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8685   -6.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5306   -7.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2791   -7.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3649   -6.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3148   -1.8026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.8104   -4.0722    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
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  5 20  1  0
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 21 22  1  0
 23 22  1  1
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 24 27  1  0
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 24 30  1  6
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 26 38  1  1
 27 39  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4594201

   ---

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: 506.55

Molecular Weight (Monoisotopic): 506.1941

AlogP: 3.82

#Rotatable Bonds: 6

Polar Surface Area: 89.52

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.55

Np Likeness Score: 1.15

References

1. da Silva Júnior EN, Jardim GAM, Jacob C, Dhawa U, Ackermann L, de Castro SL..  (2019)  Synthesis of quinones with highlighted biological applications: A critical update on the strategies towards bioactive compounds with emphasis on lapachones.,  179  [PMID:31306817] [10.1016/j.ejmech.2019.06.056]

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]

Source

Source(1):

• Scientific Literature