zoanthenol analogue

ID: ALA432577

PubChem CID: 73348231

Max Phase: Preclinical

Molecular Formula: C29H40ClNO5

Molecular Weight: 482.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)[C@H]2CC(=O)[C@H]3[C@@](C)(CC4=[N+]5C[C@H]6C[C@H](C)C[C@]5(CC[C@@]4(C)[C@@]3(C)CC(=O)O)O6)[C@@H]2C1.[Cl-]

Standard InChI:  InChI=1S/C29H39NO5.ClH/c1-16-9-20-19(21(31)10-16)11-22(32)25-26(20,3)13-23-27(4,28(25,5)14-24(33)34)6-7-29-12-17(2)8-18(35-29)15-30(23)29;/h10,17-20,25H,6-9,11-15H2,1-5H3;1H/t17-,18+,19-,20+,25-,26-,27+,28-,29-;/m0./s1

Standard InChI Key:  QQRSJGDQSCPGAJ-XAMTWZCKSA-N

Molfile:  

     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
    5.8174    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -0.7803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -0.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1786   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247   -0.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7480    0.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0576    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787    0.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611   -0.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691    1.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1514   -0.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0343   -0.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3507   -1.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878   -0.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054    0.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9338   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -1.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830    0.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434   -1.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382   -1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    0.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -1.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0482   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117    2.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231    1.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075    2.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276   -0.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3035   -1.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224    1.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844    1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    3.0399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2894   -2.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4395   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230    1.5869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243   -1.1548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882    0.3919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246   -0.7832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  2  1  0
  5 12  1  0
  6  3  1  0
  7  6  1  0
  8  5  1  0
  9  5  1  0
 10  8  1  0
 11  9  1  0
 12  3  1  0
  4 13  1  6
 14 11  1  0
 15 11  1  0
 16 19  2  0
 17  2  1  0
 18 22  1  0
 19 23  1  0
 20 17  1  0
  7 21  1  0
  4 22  1  0
 23  9  1  0
 24  4  1  0
 25 21  1  0
 26 10  2  0
 27 14  2  0
 28 25  2  0
 29 24  1  0
 30 20  1  0
  5 31  1  1
  7 32  1  6
  6 33  1  6
 34 25  1  0
 35 19  1  0
 29 36  1  6
  8 37  1  6
  9 38  1  6
 11 39  1  1
 20 13  1  0
 29 30  1  0
 18  6  1  0
  8  7  1  0
 10 15  1  0
 16 14  1  0
 20 40  1  6
M  CHG  2   1  -1   2   1
M  END

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: 482.64

Molecular Weight (Monoisotopic): 482.2901

AlogP: 4.40

#Rotatable Bonds: 2

Polar Surface Area: 83.68

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.47

CX Basic pKa: ┄

CX LogP: 0.76

CX LogD: 1.53

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.59

Np Likeness Score: 1.74

References

1. Hirai G, Oguri H, Hayashi M, Koyama K, Koizumi Y, Moharram SM, Hirama M..  (2004)  Synthesis and preliminary biological evaluation of truncated zoanthenol analogues.,  14  (10): [PMID:15109670] [10.1016/j.bmcl.2004.02.064]

Source

Source(1):

• Scientific Literature