Voratin C

ID: ALA5190887

PubChem CID: 168284833

Max Phase: Preclinical

Molecular Formula: C20H27NO5

Molecular Weight: 361.44

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]([C@@H](O)c2cccc3[n+]2CC[C@@H]3C)O[C@@]2(CC[C@H](C(=O)[O-])O2)C1

Standard InChI:  InChI=1S/C20H27NO5/c1-12-10-17(26-20(11-12)8-6-16(25-20)19(23)24)18(22)15-5-3-4-14-13(2)7-9-21(14)15/h3-5,12-13,16-18,22H,6-11H2,1-2H3/t12-,13+,16-,17-,18+,20+/m1/s1

Standard InChI Key:  GQGZKNZNDNWLML-RYNOYGMCSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -1.5130   -0.9203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7985   -0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0866   -0.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0866   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967   -2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009   -2.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7879   -1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009   -0.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5154   -2.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7985    0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360    1.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533    1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360    0.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360    2.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5158    0.7342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396   -0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6590    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    1.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820   -1.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -1.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4025   -1.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0811   -0.0908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1  9  1  0
  7 10  1  1
  2 11  1  0
 11 12  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 12 17  1  0
 14 18  1  1
 11 19  1  6
 21 22  1  0
 22 23  1  0
 16 23  1  0
 20 21  1  0
 16 20  1  1
 21 24  1  6
 24 26  2  0
 24 25  1  0
 12 27  1  6
M  CHG  2   1   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5190887

   ---

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: 361.44

Molecular Weight (Monoisotopic): 361.1889

AlogP: 0.95

#Rotatable Bonds: 3

Polar Surface Area: 82.70

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.20

CX Basic pKa: ┄

CX LogP: -2.39

CX LogD: -2.62

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: 0.78

References

1. Lee H, Moon SJ, Yoo YD, Jeong EJ, Rho JR..  (2022)  Voratins A-C: Pyridinium Alkaloids from the Marine Dinoflagellate Effrenium voratum with Inhibitory Effects on Biomarkers for Benign Prostatic Hyperplasia.,  85  (6.0): [PMID:35671052] [10.1021/acs.jnatprod.1c01190]

Source

Source(1):

• Scientific Literature