(R)-9-hydroxy-1,2,3-trimethoxy-5-methyl-11,12-dihydro-5H-benzo[e]cyclohepta[c]oxepin-10(7H)-one

ID: ALA4761501

PubChem CID: 62706886

Max Phase: Preclinical

Molecular Formula: C19H22O6

Molecular Weight: 346.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(OC)c1OC)C1=C(C=C(O)C(=O)CC1)CO[C@@H]2C

Standard InChI:  InChI=1S/C19H22O6/c1-10-13-8-16(22-2)18(23-3)19(24-4)17(13)12-5-6-14(20)15(21)7-11(12)9-25-10/h7-8,10,21H,5-6,9H2,1-4H3/t10-/m1/s1

Standard InChI Key:  YTHQSGHKJQQWKT-SNVBAGLBSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.9561   -9.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7485   -9.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3081   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024   -9.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3965   -9.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5970  -10.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3164   -8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -10.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1117   -8.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925   -8.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561  -11.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7609  -11.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6106   -7.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561   -7.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1435  -11.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7526   -7.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024  -10.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1908   -9.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1908   -7.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925  -10.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4810   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1826   -7.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9434  -12.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7806   -6.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  4  2  0
  7  1  1  0
  8  3  2  0
  9  5  2  0
 10  2  1  0
 11 14  2  0
 12  7  1  0
 13 12  1  0
 14  8  1  0
 15  8  1  0
 16  9  1  0
 17 10  1  0
 18  4  1  0
 19  6  1  0
 20 11  1  0
 21 18  1  0
 22 19  1  0
 23 20  1  0
  9 13  1  0
 15 17  1  0
 11  6  1  0
 13 24  2  0
 15 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4761501

   (5R)-9-hydroxy-1,2,3-trimethoxy-5-methyl-5,7,11,12-tetrahydrocyclohepta[d][2]benzoxepin-10-one

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: 346.38

Molecular Weight (Monoisotopic): 346.1416

AlogP: 3.36

#Rotatable Bonds: 3

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 1.87

CX LogD: 1.83

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.90

Np Likeness Score: 1.21

References

1. Gracheva IA,Shchegravina ES,Schmalz HG,Beletskaya IP,Fedorov AY.  (2020)  Colchicine Alkaloids and Synthetic Analogues: Current Progress and Perspectives.,  63  (19.0): [PMID:32432867] [10.1021/acs.jmedchem.0c00222]

Source

Source(1):

• Scientific Literature