5-(2-hydroxypropoxy)-4-oxo-8-propyl-4H-chromene-2-carboxylic acid

ID: ALA4089180

Cas Number: 58974-93-9

PubChem CID: 121899

Max Phase: Preclinical

Molecular Formula: C16H18O6

Molecular Weight: 306.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1ccc(OCC(C)O)c2c(=O)cc(C(=O)O)oc12

Standard InChI:  InChI=1S/C16H18O6/c1-3-4-10-5-6-12(21-8-9(2)17)14-11(18)7-13(16(19)20)22-15(10)14/h5-7,9,17H,3-4,8H2,1-2H3,(H,19,20)

Standard InChI Key:  YQCGBHBRCNCNLL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    5.2034   -4.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -5.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -6.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -7.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -7.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -8.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -8.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -9.4765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333   -9.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333  -10.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162  -11.1265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3462  -11.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333   -8.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3462   -8.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3462   -9.4765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0590   -8.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0590   -7.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7761   -7.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7761   -6.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4889   -7.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3462   -7.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333   -7.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  2  0
 13 14  1  0
 14 15  2  0
 16 14  1  0
 17 16  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 21 17  1  0
 22 21  1  0
  4 22  2  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089180

   4H-1-Benzopyran-2-carboxylic acid, 5-(2-hydroxypropoxy)-4-oxo-8-propyl-

Molecule Features

Natural Product: No

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: 306.31

Molecular Weight (Monoisotopic): 306.1103

AlogP: 2.20

#Rotatable Bonds: 6

Polar Surface Area: 96.97

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.17

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: -1.25

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: 0.64

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature