(1Z,4R,5E,8S,9S)-5-Methyl-11-oxo-8-(1-methylethenyl)-10-oxabicyclo[7.2.1]dodeca-1(12),5-dien-4-yl 2-Chloronicotinate

ID: ALA4467803

PubChem CID: 155532815

Max Phase: Preclinical

Molecular Formula: C21H22ClNO4

Molecular Weight: 387.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1C/C=C(\C)[C@H](OC(=O)c2cccnc2Cl)CCC2=C[C@@H]1OC2=O

Standard InChI:  InChI=1S/C21H22ClNO4/c1-12(2)15-8-6-13(3)17(9-7-14-11-18(15)27-20(14)24)26-21(25)16-5-4-10-23-19(16)22/h4-6,10-11,15,17-18H,1,7-9H2,2-3H3/b13-6+/t15-,17+,18-/m0/s1

Standard InChI Key:  RDFTZGXDOSMZMN-UFOLEPLCSA-N

Molfile:  

 
     RDKit          2D

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   24.4437   -7.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2567   -7.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5101   -6.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8481   -6.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1926   -6.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4081   -5.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4081   -6.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1094   -5.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8148   -5.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2185   -6.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2238   -5.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5165   -5.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9622   -8.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1094   -4.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9200   -6.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9172   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6284   -6.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0882   -7.3409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.3883   -6.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8171   -3.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8171   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5248   -4.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5307   -2.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5310   -1.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8228   -1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1127   -1.8698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1159   -2.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4086   -3.0942    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  6  7  1  0
  6  8  1  0
  7  5  1  0
  9  8  1  0
  9 12  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  2  0
  8 14  1  1
 10 15  1  1
 15 16  2  0
 15 17  1  0
  3 18  1  6
  9 19  1  0
 14 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4467803

   ---

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: 387.86

Molecular Weight (Monoisotopic): 387.1237

AlogP: 4.43

#Rotatable Bonds: 3

Polar Surface Area: 65.49

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: 0.66

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: 1.48

References

1. Lou LL, Ni FQ, Chen L, Shaker S, Li W, Wang R, Tang GH, Yin S..  (2019)  Germacrane Sesquiterpenoids as a New Type of Anticardiac Fibrosis Agent Targeting Transforming Growth Factor β Type I Receptor.,  62  (17): [PMID:31408333] [10.1021/acs.jmedchem.9b00708]

Source

Source(1):

• Scientific Literature