(1Z,4Z,6R,8S,9S)-10-Oxabicyclo[7.2.1]dodeca,1(12),4-dien-11-one, 6-(pyrrolidin-1-yl)-5-methyl-8-(1-methylethenyl)-

ID: ALA4469209

PubChem CID: 155533608

Max Phase: Preclinical

Molecular Formula: C19H27NO2

Molecular Weight: 301.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1C[C@@H](N2CCCC2)/C(C)=C/CCC2=C[C@@H]1OC2=O

Standard InChI:  InChI=1S/C19H27NO2/c1-13(2)16-12-17(20-9-4-5-10-20)14(3)7-6-8-15-11-18(16)22-19(15)21/h7,11,16-18H,1,4-6,8-10,12H2,2-3H3/b14-7-/t16-,17+,18-/m0/s1

Standard InChI Key:  VCBKFIVHHTZHST-LGZCINFSSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.0738  -15.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096  -15.6752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424  -14.8149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429  -14.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3744  -13.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987  -13.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7861  -13.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2586  -12.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768  -14.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565  -13.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5931  -15.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715  -12.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565  -13.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9649  -13.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798  -13.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084  -15.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6650  -14.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592  -12.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751  -11.7906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3345  -11.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854  -10.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2681  -10.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0123  -11.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  2  2  0
 17  6  1  0
 17  3  1  6
 14 12  1  0
  4 11  1  0
  9  7  1  0
 16 17  1  0
  5  9  1  1
 17  5  1  0
 10 13  1  0
  6  4  2  0
  9  1  2  0
 14  8  2  0
 15 12  1  0
 13  4  1  0
 11 16  1  0
 10  8  1  0
  5 15  1  0
 14 18  1  0
 12 19  1  6
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4469209

   ---

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: 301.43

Molecular Weight (Monoisotopic): 301.2042

AlogP: 3.63

#Rotatable Bonds: 2

Polar Surface Area: 29.54

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.62

CX Basic pKa: 10.28

CX LogP: 3.70

CX LogD: 0.91

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.58

Np Likeness Score: 1.89

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