[methyl 2,2-dimethyl-8-(3'-methyl-2'-butenyl)-2H-1-benzopyran-6-carboxylate

ID: ALA483216

PubChem CID: 15391024

Max Phase: Preclinical

Molecular Formula: C18H22O3

Molecular Weight: 286.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2c(c(CC=C(C)C)c1)OC(C)(C)C=C2

Standard InChI:  InChI=1S/C18H22O3/c1-12(2)6-7-13-10-15(17(19)20-5)11-14-8-9-18(3,4)21-16(13)14/h6,8-11H,7H2,1-5H3

Standard InChI Key:  RRVJCPRGSRFXLA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   15.6383  -13.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6383  -12.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3519  -13.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9153  -13.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3519  -12.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9153  -12.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0539  -13.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1991  -13.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0539  -12.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1991  -12.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4811  -13.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7677  -13.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4790  -14.5987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0523  -13.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9136  -11.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0482  -11.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7607  -12.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6272  -10.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6254  -10.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3390   -9.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9101   -9.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  1  0
  1  2  2  0
  1  3  1  0
 11 12  1  0
 11 13  2  0
  8 11  1  0
  1  4  1  0
 12 14  1  0
  2  5  1  0
  6 15  1  0
  2  6  1  0
  9 16  1  0
  3  7  2  0
  9 17  1  0
  4  8  2  0
 15 18  1  0
  5  9  1  0
 18 19  2  0
  6 10  2  0
 19 20  1  0
  7  9  1  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA483216

   Methyl 2,2-dimethyl-8-(3-methylbut-2-enyl)chromene-6-carboxylate

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: 286.37

Molecular Weight (Monoisotopic): 286.1569

AlogP: 4.17

#Rotatable Bonds: 3

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.62

Np Likeness Score: 2.29

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