8b-O-methylrocaglaol

ID: ALA2331822

PubChem CID: 21670100

Max Phase: Preclinical

Molecular Formula: C27H28O6

Molecular Weight: 448.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 8B-O-Methylrocaglaol | 8B-O-Methylrocaglaol|CHEMBL2331822

Canonical SMILES:  COc1ccc([C@@]23Oc4cc(OC)cc(OC)c4[C@]2(OC)[C@H](O)C[C@H]3c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H28O6/c1-29-19-12-10-18(11-13-19)26-21(17-8-6-5-7-9-17)16-24(28)27(26,32-4)25-22(31-3)14-20(30-2)15-23(25)33-26/h5-15,21,24,28H,16H2,1-4H3/t21-,24+,26-,27+/m0/s1

Standard InChI Key:  OLHDAACFTXKKEU-CYUUXAIJSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    8.5169  -12.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6724  -13.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7479  -13.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1840  -14.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0528  -14.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0898  -10.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8023  -10.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8080  -11.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8047  -12.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2945  -12.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8023  -11.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1918  -13.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9845  -10.6891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3264  -13.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5602  -11.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4097  -14.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9985  -14.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7118  -12.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5673  -12.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7872  -12.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3056  -13.4876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0961  -12.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950  -13.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757  -11.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7776  -14.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5217  -13.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0034  -13.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8065  -13.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9850  -12.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2979  -12.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3833  -13.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4058  -15.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9958  -16.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 24 30  1  0
 31  2  1  0
 29 10  1  0
 18 29  2  0
 20 19  1  0
 30  1  1  0
 26 21  1  0
 30  8  1  1
 28 26  2  0
 25  4  1  0
 16 27  2  0
  9 11  1  0
 19 10  1  1
  8  7  1  0
 17 16  1  0
  1  9  2  0
 23 31  1  0
  1 26  1  0
 22 23  2  0
 10 14  2  0
 21 20  1  0
 27 12  1  0
  5  3  2  0
 20 12  1  1
 11  6  1  0
 23 28  1  0
  9 22  1  0
 30 20  1  0
 15 24  1  0
  3 18  1  0
 14  5  1  0
 17  4  2  0
 24 13  1  6
 12 25  2  0
 19 15  1  0
 17 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2331822

   8B-O-Methylrocaglaol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 448.52

Molecular Weight (Monoisotopic): 448.1886

AlogP: 4.39

#Rotatable Bonds: 6

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.69

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: 1.50

References

1. Pan L, Acuña UM, Li J, Jena N, Ninh TN, Pannell CM, Chai H, Fuchs JR, Carcache de Blanco EJ, Soejarto DD, Kinghorn AD..  (2013)  Bioactive flavaglines and other constituents isolated from Aglaia perviridis.,  76  (3): [PMID:23301897] [10.1021/np3007588]

Source

Source(1):

• Scientific Literature