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

ID: ALA498063

PubChem CID: 10638083

Max Phase: Preclinical

Molecular Formula: C17H18O5

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(O)c3c(cc2c1)O[C@@H](C)[C@H](C)C3=O

Standard InChI:  InChI=1S/C17H18O5/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/h5-9,19H,1-4H3/t8-,9-/m0/s1

Standard InChI Key:  DALYWWKMTCBVOR-IUCAKERBSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -7.0449    0.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0437    0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351   -0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3333    1.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6155    0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6147    0.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9010   -0.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066    1.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1861    0.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4683   -0.2534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7524    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7587    0.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810    1.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885    2.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9110    2.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3392    2.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0469    2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7605   -0.2637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4698    0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486    1.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370   -0.2424    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
 13 21  1  1
  4  1  1  0
 12 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA498063

   (2S,3S)-5-hydroxy-6,8-dimethoxy-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: 302.33

Molecular Weight (Monoisotopic): 302.1154

AlogP: 3.16

#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: 8.13

CX Basic pKa: ┄

CX LogP: 3.29

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.92

Np Likeness Score: 1.74

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