R-(-)-Latifolin

ID: ALA2397757

Cas Number: 10154-42-4

PubChem CID: 340211

Max Phase: Preclinical

Molecular Formula: C17H18O4

Molecular Weight: 286.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C[C@H](c1ccccc1O)c1cc(O)c(OC)cc1OC

Standard InChI:  InChI=1S/C17H18O4/c1-4-11(12-7-5-6-8-14(12)18)13-9-15(19)17(21-3)10-16(13)20-2/h4-11,18-19H,1H2,2-3H3/t11-/m1/s1

Standard InChI Key:  OJVQOGDGFIJYPN-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   32.0772  -16.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0761  -17.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7909  -18.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5074  -17.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5044  -16.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7891  -16.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2224  -18.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2237  -19.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9363  -17.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5086  -19.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5096  -20.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2252  -20.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9414  -20.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9369  -19.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6513  -18.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3627  -16.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3625  -15.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3613  -18.2348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2174  -16.5768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2142  -15.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6493  -19.0503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  7  9  1  6
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  8  1  0
  9 15  2  0
  1 16  1  0
 16 17  1  0
  2 18  1  0
  5 19  1  0
 19 20  1  0
 14 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397757

   LATIFOLIN

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: 286.33

Molecular Weight (Monoisotopic): 286.1205

AlogP: 3.43

#Rotatable Bonds: 5

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: 0.97

References

1. Sekine N, Ashitani T, Murayama T, Shibutani S, Hattori S, Takahashi K..  (2009)  Bioactivity of latifolin and its derivatives against termites and fungi.,  57  (13): [PMID:19499920] [10.1021/jf900719p]

2. Lee C, Lee JW, Jin Q, Jang DS, Lee SJ, Lee D, Hong JT, Kim Y, Lee MK, Hwang BY..  (2013)  Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages.,  23  (14): [PMID:23743282] [10.1016/j.bmcl.2013.04.032]

3. Park SH, Yang EJ, Kim SI, Song KS..  (2014)  β-Secretase (BACE1)-inhibiting C-methylrotenoids from Abronia nana suspension cultures.,  24  (13): [PMID:24835197] [10.1016/j.bmcl.2014.04.060]

Source

Source(1):

• Scientific Literature