3R,4S-7-ethyl-4,8-dihydroxy-3,6-dimethoxy-3,4-dehydronaphthalen-1(2H)-one; Botryosphaerone E

ID: ALA4848609

PubChem CID: 156581120

Max Phase: Preclinical

Molecular Formula: C14H18O5

Molecular Weight: 266.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1c(OC)cc2c(c1O)C(=O)C[C@@H](OC)[C@H]2O

Standard InChI:  InChI=1S/C14H18O5/c1-4-7-10(18-2)5-8-12(14(7)17)9(15)6-11(19-3)13(8)16/h5,11,13,16-17H,4,6H2,1-3H3/t11-,13+/m1/s1

Standard InChI Key:  YLSOOYDKHUEZQR-YPMHNXCESA-N

Molfile:  

 
     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    2.9165   -3.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -4.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6234   -4.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216   -2.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303   -3.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -4.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392   -4.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550   -4.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7562   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0415   -2.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0369   -5.3023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4616   -4.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4593   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6192   -2.0262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -4.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -4.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087   -2.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0416   -2.0176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  1
  8 12  1  1
 12 13  1  0
  4 14  1  0
  2 15  1  0
 15 16  1  0
  1 17  1  0
 17 18  1  0
 10 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4848609

   ---

Molecule Features

Natural Product: Yes

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: 266.29

Molecular Weight (Monoisotopic): 266.1154

AlogP: 1.60

#Rotatable Bonds: 3

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 1.92

CX LogD: 1.91

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.87

Np Likeness Score: 1.90

References

1. Flores-Bocanegra L, Raja HA, Bacon JW, Maldonado AC, Burdette JE, Pearce CJ, Oberlies NH..  (2021)  Cytotoxic Naphthoquinone Analogues, Including Heterodimers, and Their Structure Elucidation Using LR-HSQMBC NMR Experiments.,  84  (3.0): [PMID:33006889] [10.1021/acs.jnatprod.0c00856]

Source

Source(1):

• Scientific Literature