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

ID: ALA497901

PubChem CID: 10710646

Max Phase: Preclinical

Molecular Formula: C17H18O6

Molecular Weight: 318.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(O)c3c(c(OC)c2c1)O[C@@H](C)CC3=O

Standard InChI:  InChI=1S/C17H18O6/c1-8-5-11(18)14-15(19)13-10(16(22-4)17(14)23-8)6-9(20-2)7-12(13)21-3/h6-8,19H,5H2,1-4H3/t8-/m0/s1

Standard InChI Key:  DWGSEYZQYRDTJV-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   13.1034    1.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1022    0.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8166    0.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8148    1.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5298    1.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5306    0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2454    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2397    1.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9552    1.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9616    0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6805    0.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3978    0.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3914    1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6678    1.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6604    2.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2354    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8124    2.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0971    3.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3878    0.2814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6741    0.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1144    0.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2460   -0.5380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9604   -0.9496    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  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
  4  1  1  0
  7 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA497901

   (2S)-5-hydroxy-6,8,10-trimethoxy-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: 318.33

Molecular Weight (Monoisotopic): 318.1103

AlogP: 2.92

#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: 8.65

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.94

Np Likeness Score: 1.66

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