(2S)-5-hydroxy-6,8-dimethoxy-2-methyl-4H-2,3-dihydronaphto[2,3-b]-pyran-4-one

ID: ALA497723

PubChem CID: 10755767

Max Phase: Preclinical

Molecular Formula: C16H16O5

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(O)c3c(cc2c1)O[C@@H](C)CC3=O

Standard InChI:  InChI=1S/C16H16O5/c1-8-4-11(17)15-13(21-8)6-9-5-10(19-2)7-12(20-3)14(9)16(15)18/h5-8,18H,4H2,1-3H3/t8-/m0/s1

Standard InChI Key:  AHQXDHIRTWHABS-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.6681    1.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6670    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3789    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0933    1.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0940    0.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8083    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8027    1.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5175    1.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5239    0.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2422    0.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9588    0.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9525    1.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2295    1.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2220    2.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7983    2.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3764    2.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6618    2.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532    0.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400    0.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6748    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  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  1  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  6
M  END

Alternative Forms

1. Parent:

   

   ALA497723

   (2S)-5-hydroxy-6,8-dimethoxy-2-methyl-4H-2,3-dihydronaphtho[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: 288.30

Molecular Weight (Monoisotopic): 288.0998

AlogP: 2.92

#Rotatable Bonds: 2

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.14

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.92

Np Likeness Score: 1.51

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