Obovatin 5-methyl ether

ID: ALA2230140

Cas Number: 69640-78-4

PubChem CID: 155236

Max Phase: Preclinical

Molecular Formula: C21H20O4

Molecular Weight: 336.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(c3c1C(=O)C[C@@H](c1ccccc1)O3)C=CC(C)(C)O2

Standard InChI:  InChI=1S/C21H20O4/c1-21(2)10-9-14-17(25-21)12-18(23-3)19-15(22)11-16(24-20(14)19)13-7-5-4-6-8-13/h4-10,12,16H,11H2,1-3H3/t16-/m0/s1

Standard InChI Key:  ITOTUSMHIQFNHJ-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    0.6480   -1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -1.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601   -1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1766   -3.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -4.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5915   -3.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -3.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -4.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0162   -3.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174   -3.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -2.6821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244   -2.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4314   -3.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1396   -2.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1421   -1.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4304   -1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251   -1.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1778   -3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -2.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783   -1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -1.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -2.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981   -5.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -5.1452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1765   -5.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 18  4  1  0
  4  5  2  0
  5  7  1  0
  6 19  1  0
  6  7  2  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 12  1  6
 18 19  2  0
 18 22  1  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
  2 22  1  0
  8 23  2  0
  5 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2230140

   OBOVATIN 5-METHYL ETHER

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: 336.39

Molecular Weight (Monoisotopic): 336.1362

AlogP: 4.59

#Rotatable Bonds: 2

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: 2.29

References

1. Belmain SR, Amoah BA, Nyirenda SP, Kamanula JF, Stevenson PC..  (2012)  Highly variable insect control efficacy of Tephrosia vogelii chemotypes.,  60  (40): [PMID:22970736] [10.1021/jf3032217]

Source

Source(1):

• Scientific Literature