Andrographolide-14-propionate

ID: ALA4213713

PubChem CID: 145966285

Max Phase: Preclinical

Molecular Formula: C23H34O6

Molecular Weight: 406.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1OC(=O)CC

Standard InChI:  InChI=1S/C23H34O6/c1-5-20(26)29-17-12-28-21(27)15(17)7-8-16-14(2)6-9-18-22(16,3)11-10-19(25)23(18,4)13-24/h7,16-19,24-25H,2,5-6,8-13H2,1,3-4H3/b15-7+/t16-,17-,18+,19-,22+,23+/m1/s1

Standard InChI Key:  MJVLDMCIIODBBB-WPWPTVPKSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   13.7313   -7.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3268   -6.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9179   -7.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252   -5.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252   -6.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3305   -5.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0358   -5.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0323   -6.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7343   -6.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4444   -6.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4478   -5.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7413   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9181   -6.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0285   -4.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7436   -4.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4525   -4.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4548   -3.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1159   -2.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8656   -1.9933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0484   -1.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7938   -2.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0164   -3.0192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8922   -3.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1577   -5.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3204   -8.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2389   -7.2969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4096   -2.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6321   -2.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5802   -1.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0253   -2.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  6
  7 14  1  6
 12 15  1  6
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 21 22  1  6
 18 23  2  0
 11 24  2  0
  1 25  1  0
  8 26  1  1
 22 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213713

   ---

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: 406.52

Molecular Weight (Monoisotopic): 406.2355

AlogP: 2.92

#Rotatable Bonds: 5

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.80

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 2.89

References

1. Patil HS, Jadhav DD, Paul A, Mulani FA, Karegaonkar SJ, Thulasiram HV..  (2018)  Regioselective and efficient enzymatic synthesis of antimicrobial andrographolide derivatives.,  28  (6): [PMID:29475585] [10.1016/j.bmcl.2018.01.007]

Source

Source(1):

• Scientific Literature