Cryptobeilic acid B

ID: ALA2334426

PubChem CID: 71521967

Max Phase: Preclinical

Molecular Formula: C20H28O3

Molecular Weight: 316.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cryptobeilic Acid B | hexyl(hydroxy)[?]carboxylic acid|Cryptobeilic Acid B|CHEMBL2334426

Canonical SMILES:  CCCCCC[C@@H]1[C@H]2C=C[C@H]3C(C(=O)O)=C[C@@H](O)[C@@H]4C[C@@H]1[C@@H]2[C@H]43

Standard InChI:  InChI=1S/C20H28O3/c1-2-3-4-5-6-11-12-7-8-13-15(20(22)23)10-17(21)16-9-14(11)18(12)19(13)16/h7-8,10-14,16-19,21H,2-6,9H2,1H3,(H,22,23)/t11-,12-,13+,14+,16+,17-,18-,19+/m1/s1

Standard InChI Key:  CFVWGWLCFBEENY-YCJWGMIRSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.1163   -5.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1163   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8216   -5.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5269   -5.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9355   -6.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9390   -5.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2324   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8216   -4.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5293   -4.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1139   -4.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7342   -4.9197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2274   -6.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5234   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8217   -6.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0781   -7.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0080   -7.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2360   -7.5116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7272   -6.3105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2212   -6.1207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7524   -6.5334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7206   -7.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0065   -8.5104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4249   -7.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4091   -6.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4182   -8.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1226   -8.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8336   -8.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5379   -8.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2490   -8.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2 14  1  0
  4  3  1  0
  4 13  1  0
  4  7  1  0
 12  5  1  0
  5  6  1  0
  6  7  2  0
  3  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  1
 13 14  1  0
 12 13  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 14 17  1  6
 13 18  1  1
 12 19  1  1
  5 20  1  1
  5 21  1  0
 21 16  1  0
 16 22  1  1
 21 23  1  1
  2 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2334426

   CRYPTOBEILIC ACID B

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: 316.44

Molecular Weight (Monoisotopic): 316.2038

AlogP: 3.64

#Rotatable Bonds: 6

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.27

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 0.53

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: 2.71

References

1. Talontsi FM, Lamshöft M, Bauer JO, Razakarivony AA, Andriamihaja B, Strohmann C, Spiteller M..  (2013)  Antibacterial and antiplasmodial constituents of Beilschmiedia cryptocaryoides.,  76  (1): [PMID:23320609] [10.1021/np300773x]

Source

Source(1):

• Scientific Literature