((1R,5aS,6R,9aS)-1,5a-dimethyl-7-methylene-3-oxo-6-((E)-2-(2-oxo-2,5-dihydrofuran-3-yl)ethenyl)decahydro-1H-benzo[c]azepin-1-yl)methyl benzoate

ID: ALA4592431

PubChem CID: 155569173

Max Phase: Preclinical

Molecular Formula: C27H31NO5

Molecular Weight: 449.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@@](C)(CCC(=O)N[C@@]2(C)COC(=O)c2ccccc2)[C@@H]1/C=C/C1=CCOC1=O

Standard InChI:  InChI=1S/C27H31NO5/c1-18-9-12-22-26(2,21(18)11-10-20-14-16-32-24(20)30)15-13-23(29)28-27(22,3)17-33-25(31)19-7-5-4-6-8-19/h4-8,10-11,14,21-22H,1,9,12-13,15-17H2,2-3H3,(H,28,29)/b11-10+/t21-,22+,26+,27+/m1/s1

Standard InChI Key:  LCKJDMDNIAQVMC-IYFJMWNJSA-N

Molfile:  

 
     RDKit          2D

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   15.9766   -5.8864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   17.6315   -6.3394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   19.2384   -1.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.1689   -1.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2690   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5405   -4.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1722   -6.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5808   -7.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3980   -7.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1722   -8.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.6166   -6.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  2  0
 34 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4592431

   ---

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: 449.55

Molecular Weight (Monoisotopic): 449.2202

AlogP: 4.14

#Rotatable Bonds: 5

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.74

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.17

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: 2.05

References

1. Wang W, Wu Y, Yang K, Wu C, Tang R, Li H, Chen L..  (2019)  Synthesis of novel andrographolide beckmann rearrangement derivatives and evaluation of their HK2-related anti-inflammatory activities.,  173  [PMID:31009914] [10.1016/j.ejmech.2019.04.022]

Source

Source(1):

• Scientific Literature