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

ID: ALA4529216

PubChem CID: 155545169

Max Phase: Preclinical

Molecular Formula: C22H23NO6

Molecular Weight: 397.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1C/C=C(\C)[C@H](OC(=O)c2ccc([N+](=O)[O-])cc2)CCC2=C[C@@H]1OC2=O

Standard InChI:  InChI=1S/C22H23NO6/c1-13(2)18-10-4-14(3)19(11-7-16-12-20(18)29-22(16)25)28-21(24)15-5-8-17(9-6-15)23(26)27/h4-6,8-9,12,18-20H,1,7,10-11H2,2-3H3/b14-4+/t18-,19+,20-/m0/s1

Standard InChI Key:  AXWUAGBXSRZAOF-ZAIWJUQASA-N

Molfile:  

 
     RDKit          2D

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   31.4104   -8.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2235   -8.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4768   -7.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8149   -7.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1594   -7.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3749   -6.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3749   -7.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0761   -5.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7816   -6.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1853   -7.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1906   -6.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4832   -5.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9290   -8.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0761   -5.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8868   -7.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8839   -8.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5952   -7.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0549   -8.1374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.3551   -6.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7839   -4.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7839   -3.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4916   -5.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4974   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4978   -2.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7895   -2.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0795   -2.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0826   -3.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7879   -1.4360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0796   -1.0283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4950   -1.0264    0.0000 O   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
 28 29  2  0
 28 30  1  0
 25 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4529216

   ---

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: 397.43

Molecular Weight (Monoisotopic): 397.1525

AlogP: 4.29

#Rotatable Bonds: 4

Polar Surface Area: 95.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: ┄

CX LogP: 5.02

CX LogD: 5.02

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.33

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