(2S,3S)-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-4H-2,3-dihydronaphtho[2,3-b]-pyran-4-one

ID: ALA497708

PubChem CID: 10544539

Max Phase: Preclinical

Molecular Formula: C18H20O6

Molecular Weight: 332.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(O)c3c(c(OC)c2c1)O[C@@H](C)[C@H](C)C3=O

Standard InChI:  InChI=1S/C18H20O6/c1-8-9(2)24-18-14(15(8)19)16(20)13-11(17(18)23-5)6-10(21-3)7-12(13)22-4/h6-9,20H,1-5H3/t8-,9-/m0/s1

Standard InChI Key:  KRQMXQZQIPIILU-IUCAKERBSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -0.1930    1.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1942    0.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202   -0.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    1.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2332    1.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340    0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9433    1.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    1.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6650    0.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3839   -0.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010    0.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0946    1.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712    1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    2.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389    2.3745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    2.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1993    2.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085   -0.1058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6221    0.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8059    1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175   -0.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -0.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -1.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 13 21  1  1
  4  1  1  0
 12 22  1  6
  7 23  1  0
  2  3  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA497708

   (2S,3S)-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-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: 332.35

Molecular Weight (Monoisotopic): 332.1260

AlogP: 3.17

#Rotatable Bonds: 3

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.64

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.11

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.93

Np Likeness Score: 1.85

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