Dendrillic acid B

ID: ALA5290176

Max Phase: Preclinical

Molecular Formula: C21H27NO5

Molecular Weight: 373.45

Names and Identifiers

Canonical SMILES:  C[C@H]1c2c([C@@]3(C)CCCC(C)(C)C3)ccc(C(=O)O)c2C(=O)N1CC(=O)O

Standard InChI:  InChI=1S/C21H27NO5/c1-12-16-14(21(4)9-5-8-20(2,3)11-21)7-6-13(19(26)27)17(16)18(25)22(12)10-15(23)24/h6-7,12H,5,8-11H2,1-4H3,(H,23,24)(H,26,27)/t12-,21-/m0/s1

Standard InChI Key:  GSUIBTCHWHWBNN-QKVFXAPYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.7531   -0.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386    0.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241   -0.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241   -0.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386   -1.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -0.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6099    0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097    1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1027    1.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173    1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8188    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834   -0.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -0.9660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -2.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -0.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311    0.0023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    1.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    2.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2457    1.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4517   -2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2997   -1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  7  3  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
  7 12  1  0
 12 11  2  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 13  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 14 20  2  0
 10 21  1  0
 21 22  2  0
 21 23  1  0
  3 24  1  1
  5 25  1  0
  5 26  1  0
 13 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5290176

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 373.45

Molecular Weight (Monoisotopic): 373.1889

AlogP: 3.84

#Rotatable Bonds: 4

Polar Surface Area: 94.91

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.20

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: -2.98

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.84

Np Likeness Score: 0.91

References

1. Sala S, James PJC, Nealon GL, Fromont J, Gomez O, Vuong D, Lacey E, Flematti GR..  (2023)  Dendrillic Acids A and B: Nitrogenous, Rearranged Spongian Nor-Diterpenes from a Dendrilla sp. Marine Sponge.,  86  (3): [PMID:36926864] [10.1021/acs.jnatprod.2c01087]

Source

Source(1):

• Scientific Literature