(R)-11-[(2R,8R,10S,11S)-2,8-Dihydroxy-4-methyl-7-oxo-11-((Z)-pent-2-enyl)-9-oxa-4-aza-tricyclo[6.3.1.0*1,5*]dodec-5-en-10-yl]-9-hydroxy-10-oxo-undecanoic acid

ID: ALA459340

PubChem CID: 44588342

Max Phase: Preclinical

Molecular Formula: C27H41NO8

Molecular Weight: 507.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC/C=C\C[C@@H]1[C@H](CC(=O)[C@H](O)CCCCCCCC(=O)O)O[C@]2(O)CC13C(=CC2=O)N(C)C[C@@H]3O

Standard InChI:  InChI=1S/C27H41NO8/c1-3-4-8-11-18-21(14-20(30)19(29)12-9-6-5-7-10-13-25(33)34)36-27(35)17-26(18)22(15-23(27)31)28(2)16-24(26)32/h4,8,15,18-19,21,24,29,32,35H,3,5-7,9-14,16-17H2,1-2H3,(H,33,34)/b8-4-/t18-,19-,21+,24+,26?,27-/m1/s1

Standard InChI Key:  HXDCZOUEOAHBBC-PSLLBRFOSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3588  -24.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532  -24.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532  -23.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588  -23.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750  -22.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458  -22.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3723  -22.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750  -23.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906  -22.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929  -21.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084  -21.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218  -21.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9374  -21.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762  -21.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364  -21.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3325  -20.2822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528  -21.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566  -22.3414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7653  -21.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817  -21.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942  -21.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106  -21.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6232  -21.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3396  -21.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0521  -21.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7685  -21.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7738  -22.3158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4825  -21.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708  -24.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708  -23.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598  -23.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475  -23.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598  -24.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671  -24.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148  -25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792  -22.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0
  1  2  1  0
 17 18  1  1
  3  8  1  6
 17 19  1  0
  2  3  1  0
 19 20  1  0
  5  9  1  6
 20 21  1  0
  3  4  1  0
 21 22  1  0
  9 10  1  0
 22 23  1  0
 23 24  1  0
 10 11  2  0
 24 25  1  0
 30  5  1  0
 25 26  1  0
 11 12  1  0
 30  4  1  0
 26 27  1  0
 26 28  2  0
 29 30  1  0
 12 13  1  0
  3  6  1  0
  7 14  1  6
  5  7  1  0
 14 15  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 29  1  2  0
  2 34  2  0
 15 16  2  0
 33 35  1  0
  6  7  1  0
 31 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA459340

   (9R)-11-[(2R,8R,10S,11S)-2,8-dihydroxy-4-methyl-7-oxo-11-[(Z)-pent-2-enyl]-9-oxa-4-azatricyclo[6.3.1.01,5]dodec-5-en-10-yl]-9-hydroxy-10-oxoundecanoic acid

Molecule Features

Natural Product: No

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: 507.62

Molecular Weight (Monoisotopic): 507.2832

AlogP: 2.33

#Rotatable Bonds: 14

Polar Surface Area: 144.60

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.68

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: 0.07

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.21

Np Likeness Score: 1.46

References

1. Kai K, Takeuchi J, Kataoka T, Yokoyama M, Watanabe N..  (2008)  Structure and biological activity of novel FN analogs as flowering inducers.,  16  (23): [PMID:18952445] [10.1016/j.bmc.2008.10.014]

Source

Source(1):

• Scientific Literature