5-hydroxy-6,8-dimethoxy-2,3-dimethyl-4H-naphthol[2,3-b]-pyran-4-one

ID: ALA504766

PubChem CID: 10685604

Max Phase: Preclinical

Molecular Formula: C17H16O5

Molecular Weight: 300.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(O)c3c(=O)c(C)c(C)oc3cc2c1

Standard InChI:  InChI=1S/C17H16O5/c1-8-9(2)22-13-6-10-5-11(20-3)7-12(21-4)14(10)17(19)15(13)16(8)18/h5-7,19H,1-4H3

Standard InChI Key:  FZYRENRMDAPHEM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -6.3199   -3.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3187   -4.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6026   -4.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6044   -2.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8909   -3.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8901   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766   -4.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822   -2.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681   -3.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -4.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443   -4.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0285   -4.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -3.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7569   -2.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7644   -2.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1866   -2.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6068   -2.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219   -1.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0354   -4.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7445   -4.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -4.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249   -2.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  5  6  1  0
  3  6  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  7 10  2  0
  8 16  1  0
  1  2  2  0
  4 17  1  0
  9  8  2  0
 17 18  1  0
  8  5  1  0
  2 19  1  0
  9 10  1  0
 19 20  1  0
  5  4  2  0
 12 21  1  0
  4  1  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA504766

   5-hydroxy-6,8-dimethoxy-2,3-dimethyl-4H-naphtho[2,3-b]pyran-4-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 300.31

Molecular Weight (Monoisotopic): 300.0998

AlogP: 3.29

#Rotatable Bonds: 2

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.80

CX Basic pKa: ┄

CX LogP: 3.29

CX LogD: 2.61

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: 1.22

References

1. Macías M, Ulloa M, Gamboa A, Mata R..  (2000)  Phytotoxic compounds from the new coprophilous fungus guanomyces polythrix.,  63  (6): [PMID:10869195] [10.1021/np990534h]

Source

Source(1):

• Scientific Literature