Cryptobeilic acid C

ID: ALA2334427

PubChem CID: 71521968

Max Phase: Preclinical

Molecular Formula: C22H20O5

Molecular Weight: 364.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cryptobeilic Acid C | Cryptobeilic Acid C|CHEMBL2334427|1,3-benzodioxol-5-ylmethyl(oxo)[?]carboxylic acid

Canonical SMILES:  O=C(O)C1=CC(=O)[C@@H]2C[C@H]3[C@H](Cc4ccc5c(c4)OCO5)[C@H]4C=C[C@@H]1[C@@H]2[C@H]43

Standard InChI:  InChI=1S/C22H20O5/c23-17-8-15(22(24)25)12-3-2-11-13(14-7-16(17)21(12)20(11)14)5-10-1-4-18-19(6-10)27-9-26-18/h1-4,6,8,11-14,16,20-21H,5,7,9H2,(H,24,25)/t11-,12+,13-,14+,16+,20-,21+/m1/s1

Standard InChI Key:  WIFSTHBLXUMVNG-OQBXOKOHSA-N

Molfile:  

     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
    6.2816  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9869  -11.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6922  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1008  -12.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1043  -12.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3977  -11.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9869  -10.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6946  -10.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792  -10.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995  -11.3623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3927  -13.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6887  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9870  -13.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2434  -14.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1733  -14.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4013  -13.9542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925  -12.7531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3865  -12.5633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9177  -12.9760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8859  -13.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1718  -14.9530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6044  -14.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5744  -13.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6265  -14.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9296  -15.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513  -16.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3438  -15.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9900  -16.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3689  -16.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6729  -16.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8664  -17.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6815  -17.4488    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  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 31  2  0
 30 28  2  0
 28 25  1  0
 30 31  1  0
 29 30  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2334427

   CRYPTOBEILIC ACID C

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: 364.40

Molecular Weight (Monoisotopic): 364.1311

AlogP: 2.85

#Rotatable Bonds: 3

Polar Surface Area: 72.83

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: ┄

CX LogP: 3.08

CX LogD: -0.34

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.84

Np Likeness Score: 2.10

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