methyl 4-hydroxy-3-(3'-methyl-1'-oxo-2'-butenyl)benzoate

ID: ALA447071

PubChem CID: 11701427

Max Phase: Preclinical

Molecular Formula: C13H14O4

Molecular Weight: 234.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: methyl taboganate | methyl taboganate|CHEMBL447071

Canonical SMILES:  COC(=O)c1ccc(O)c(C(=O)C=C(C)C)c1

Standard InChI:  InChI=1S/C13H14O4/c1-8(2)6-12(15)10-7-9(13(16)17-3)4-5-11(10)14/h4-7,14H,1-3H3

Standard InChI Key:  MYNYNZOFYYKQDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    5.3882  -12.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869  -12.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0998  -13.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191  -12.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8159  -12.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0979  -11.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985  -14.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835  -14.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8123  -14.6130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0939  -10.8937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697  -14.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5283  -11.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2449  -12.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5243  -10.8865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9572  -11.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6737  -12.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9531  -10.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  2  0
  3  7  1  0
  4  5  1  0
  6 10  1  0
  2  3  1  0
  8 11  1  0
  5  6  2  0
  5 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 12 14  2  0
  3  4  2  0
 13 15  2  0
 15 16  1  0
  7  8  1  0
 15 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA447071

   METHYL TABOGANATE

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: 234.25

Molecular Weight (Monoisotopic): 234.0892

AlogP: 2.33

#Rotatable Bonds: 3

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.23

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 2.12

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.49

Np Likeness Score: 0.70

References

1. Lago JH, Ramos CS, Casanova DC, Morandim Ade A, Bergamo DC, Cavalheiro AJ, Bolzani Vda S, Furlan M, Guimarães EF, Young MC, Kato MJ..  (2004)  Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum.,  67  (11): [PMID:15568762] [10.1021/np030530j]

Source

Source(1):

• Scientific Literature