(2S,4R)-4,5,6,7-tetramethoxyflavan

ID: ALA1081775

PubChem CID: 44614520

Max Phase: Preclinical

Molecular Formula: C19H22O5

Molecular Weight: 330.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (2S,4R)-4,5,6,7-Tetramethoxyflavan | CHEMBL1081775|(2S,4R)-4,5,6,7-tetramethoxyflavan

Canonical SMILES:  COc1cc2c(c(OC)c1OC)[C@H](OC)C[C@@H](c1ccccc1)O2

Standard InChI:  InChI=1S/C19H22O5/c1-20-14-10-13(12-8-6-5-7-9-12)24-15-11-16(21-2)18(22-3)19(23-4)17(14)15/h5-9,11,13-14H,10H2,1-4H3/t13-,14+/m0/s1

Standard InChI Key:  IMKNBXLCVBCZGQ-UONOGXRCSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.2095    1.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2084    1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224    0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9206    2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6352    1.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3571    0.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0767    1.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0732    1.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3502    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7846    2.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4998    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2117    2.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2096    3.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4896    3.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7807    3.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3592   -0.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9209   -0.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    0.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4958    2.3514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7810    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2066   -0.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0741   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
 16 11  1  0
  9 11  1  6
  4  1  1  0
  7 17  1  1
  5 10  1  0
  3 18  1  0
  6  7  1  0
  2 19  1  0
  7  8  1  0
  1 20  1  0
  8  9  1  0
 19 21  1  0
  9 10  1  0
 20 22  1  0
  5  6  1  0
 18 23  1  0
 17 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1081775

   (2S,4R)-4,5,6,7-tetramethoxyflavan

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: 330.38

Molecular Weight (Monoisotopic): 330.1467

AlogP: 3.92

#Rotatable Bonds: 5

Polar Surface Area: 46.15

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: 1.38

References

1. Lenta BN, Tantangmo F, Devkota KP, Wansi JD, Chouna JR, Soh RC, Neumann B, Stammler HG, Tsamo E, Sewald N..  (2009)  Bioactive constituents of the stem bark of Beilschmiedia zenkeri.,  72  (12): [PMID:19904919] [10.1021/np900341f]

Source

Source(1):

• Scientific Literature