19-O-Acetylclinopodiolide A

ID: ALA4513604

PubChem CID: 155538845

Max Phase: Preclinical

Molecular Formula: C23H30O6

Molecular Weight: 402.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(C(C)C)cc2c(c1O)[C@]13CCC[C@](C)([C@H](OC(C)=O)OC1=O)[C@@H]3CC2

Standard InChI:  InChI=1S/C23H30O6/c1-12(2)15-11-14-7-8-16-22(4)9-6-10-23(16,17(14)18(25)19(15)27-5)20(26)29-21(22)28-13(3)24/h11-12,16,21,25H,6-10H2,1-5H3/t16-,21+,22-,23+/m0/s1

Standard InChI Key:  UNQVCHJFBNMSGB-AZIXLERZSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   12.6208   -4.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3342   -4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6162   -4.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252   -5.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0522   -4.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3342   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7613   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7524   -4.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0522   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4746   -5.3069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9116   -6.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3387   -6.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4969   -6.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0522   -5.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4837   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9161   -4.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0522   -2.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1892   -5.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1892   -4.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4883   -2.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1973   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6787   -6.6047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3219   -6.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3455   -2.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8491   -3.6881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7298   -7.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9676   -6.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004   -7.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9727   -6.0117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6187   -3.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  1
  4  1  1  0
  5  2  2  0
  6  2  1  0
  7  9  1  0
  8  5  1  0
  9  6  2  0
 10  3  1  0
 11  4  1  0
 12  4  1  0
 13 11  1  0
 14 12  1  0
 15  7  1  0
 16  1  1  0
 17  9  1  0
 18 19  1  0
 19 16  1  0
 20 15  1  0
 21 15  1  0
  4 22  1  6
 11 18  1  0
  5 14  1  0
 10 13  1  0
  8  7  2  0
 11 23  1  6
 17 24  1  0
  3 25  2  0
 13 26  1  6
 26 27  1  0
 27 28  1  0
 27 29  2  0
  6 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513604

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 402.49

Molecular Weight (Monoisotopic): 402.2042

AlogP: 3.96

#Rotatable Bonds: 3

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: ┄

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.77

Np Likeness Score: 2.36

References

1. Bustos-Brito C, Joseph-Nathan P, Burgueño-Tapia E, Martínez-Otero D, Nieto-Camacho A, Calzada F, Yépez-Mulia L, Esquivel B, Quijano L..  (2019)  Structure and Absolute Configuration of Abietane Diterpenoids from Salvia clinopodioides: Antioxidant, Antiprotozoal, and Antipropulsive Activities.,  82  (5): [PMID:31063376] [10.1021/acs.jnatprod.8b00952]

Source

Source(1):

• Scientific Literature