15-hydroxy-16-oxo-15,16H-strictic acid

ID: ALA4243120

PubChem CID: 145983045

Max Phase: Preclinical

Molecular Formula: C20H26O5

Molecular Weight: 346.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H](C)[C@@](C)(CCC2=CC(O)OC2=O)C/C=C\C=C/1C(=O)O

Standard InChI:  InChI=1S/C20H26O5/c1-13-7-8-14(2)20(3,10-5-4-6-16(13)18(22)23)11-9-15-12-17(21)25-19(15)24/h4-6,12,14,17,21H,1,7-11H2,2-3H3,(H,22,23)/b5-4-,16-6+/t14-,17?,20+/m0/s1

Standard InChI Key:  DYQVUHJGPRMPQI-PNOCIDKFSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   34.2587   -5.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2576   -6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9656   -7.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9638   -5.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6724   -5.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6713   -6.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3775   -7.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0894   -6.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0905   -5.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3798   -5.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9673   -7.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2604   -8.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6758   -8.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3798   -4.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0875   -4.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0875   -3.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0831   -5.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7992   -5.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7500   -2.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4975   -2.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6802   -2.1185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4278   -2.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9778   -1.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6508   -3.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3733   -6.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 11 13  2  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 10 17  1  1
  9 18  1  1
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 16  1  0
 20 23  1  0
 22 24  2  0
  6 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4243120

   ---

Molecule Features

Natural Product: Yes

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: 346.42

Molecular Weight (Monoisotopic): 346.1780

AlogP: 3.52

#Rotatable Bonds: 4

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.63

CX Basic pKa: ┄

CX LogP: 4.07

CX LogD: 1.38

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: 2.68

References

1. Qiao Y, Zheng H, Li L, Zhang J, Li Y, Li S, Zhu R, Zhou J, Zhao S, Jiang Y, Lou H..  (2018)  Terpenoids with vasorelaxant effects from the Chinese liverwort Scapania carinthiaca.,  26  (14): [PMID:30049584] [10.1016/j.bmc.2018.07.035]

Source

Source(1):

• Scientific Literature