Voratin A

ID: ALA5204185

PubChem CID: 168293994

Max Phase: Preclinical

Molecular Formula: C22H29NO5

Molecular Weight: 387.48

Names and Identifiers

Canonical SMILES:  C=C1C[C@H](C(=O)[O-])O[C@@]2(C1)C[C@@H](C)C[C@H]([C@@H](O)c1cccc3[n+]1CC[C@@H]3C)O2

Standard InChI:  InChI=1S/C22H29NO5/c1-13-9-18(20(24)17-6-4-5-16-15(3)7-8-23(16)17)27-22(11-13)12-14(2)10-19(28-22)21(25)26/h4-6,13,15,18-20,24H,2,7-12H2,1,3H3/t13-,15-,18+,19+,20-,22+/m0/s1

Standard InChI Key:  LRAXFBCYSKSXFI-AXPVUZSZSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.8717   -0.9204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452   -0.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452   -1.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554   -2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717   -1.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596   -0.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596   -2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1465   -1.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571    0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772    1.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9947    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9947    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772    0.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119    1.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291   -0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -0.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9947   -0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291   -1.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946   -1.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465    1.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772    2.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    0.7342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8740   -2.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -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
  1  6  1  0
  6  5  2  0
  1  7  1  0
  6  8  1  0
  8  9  1  0
  9  7  1  0
  2 10  1  0
 10 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 11 16  1  0
 15 17  1  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
 15 21  1  6
 20 21  1  0
 20 22  1  6
 22 23  2  0
 22 24  1  0
 18 25  2  0
 13 26  1  6
 10 27  1  6
  8 28  1  1
 11 29  1  6
M  CHG  2   1   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5204185

   ---

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: 387.48

Molecular Weight (Monoisotopic): 387.2046

AlogP: 1.51

#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: 3.32

CX Basic pKa: ┄

CX LogP: -2.01

CX LogD: -2.24

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 0.84

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