(1Z,5E,8S,9S)-10-Oxabicyclo[7.2.1]dodeca-5,12-dien-11-one, 4-(((furan-2-carbonyl)oxy)imino)-5-methyl-8-(1-methylethenyl)-

ID: ALA4465221

PubChem CID: 155531018

Max Phase: Preclinical

Molecular Formula: C20H21NO5

Molecular Weight: 355.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1C/C=C(C)/C(=N\OC(=O)c2ccco2)CCC2=C[C@@H]1OC2=O

Standard InChI:  InChI=1S/C20H21NO5/c1-12(2)15-8-6-13(3)16(9-7-14-11-18(15)25-19(14)22)21-26-20(23)17-5-4-10-24-17/h4-6,10-11,15,18H,1,7-9H2,2-3H3/b13-6+,21-16-/t15-,18-/m0/s1

Standard InChI Key:  LVSWCOIEJHPOAM-TURNLRKXSA-N

Molfile:  

 
     RDKit          2D

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   35.5131   -8.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5202   -9.2717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6736   -8.4030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.7559   -7.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8070   -7.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4180   -7.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2323   -7.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6707   -6.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5161   -7.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9619   -6.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0084   -8.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0973   -6.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9619   -7.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3839   -6.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8124   -6.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8317   -8.6069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0907   -7.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6696   -5.3421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9656   -7.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3836   -4.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3825   -4.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0965   -3.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6673   -3.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8541   -4.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4054   -3.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9919   -2.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1851   -2.8683    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  2  0
  4 11  1  0
  9  7  1  0
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  5  9  1  1
 17  5  1  0
 10 13  1  0
  6  4  2  0
  9  1  2  0
 14  8  1  0
 15 12  1  0
 13  4  1  0
 11 16  1  0
 10  8  1  0
  5 15  1  0
  8 18  2  0
 14 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4465221

   ---

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: 355.39

Molecular Weight (Monoisotopic): 355.1420

AlogP: 3.97

#Rotatable Bonds: 3

Polar Surface Area: 78.10

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: 1.50

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.35

Np Likeness Score: 1.16

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