(+/-)-5-hydroxy-6-(1-hydroxyethyl)-2,7-dimethoxy-1,4-naphthalenedione

ID: ALA4874510

Cas Number: 86108-17-0

PubChem CID: 158914

Max Phase: Preclinical

Molecular Formula: C14H14O6

Molecular Weight: 278.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)c2c(cc(OC)c(C(C)O)c2O)C1=O

Standard InChI:  InChI=1S/C14H14O6/c1-6(15)11-9(19-2)4-7-12(14(11)18)8(16)5-10(20-3)13(7)17/h4-6,15,18H,1-3H3

Standard InChI Key:  DUFFAWHPHNGPDG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    3.7173  -13.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162  -14.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4306  -14.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288  -12.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438  -13.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425  -14.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8590  -14.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5814  -14.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5826  -13.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8614  -12.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567  -15.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942  -14.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2919  -15.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264  -12.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018  -14.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2880  -14.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032  -12.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892  -13.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8615  -12.1135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030  -12.1226    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  2  0
  9 10  1  0
  7 11  2  0
  8 12  1  0
 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
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874510

   5-Hydroxy-6-(1-hydroxyethyl)-2,7-dimethoxy-1,4-naphthoquinone

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: 278.26

Molecular Weight (Monoisotopic): 278.0790

AlogP: 1.36

#Rotatable Bonds: 3

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: 0.93

CX LogD: 0.89

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.87

Np Likeness Score: 1.88

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