6-Methoxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one

ID: ALA529210

Chembl Id: CHEMBL529210

Cas Number: 6054-10-0

PubChem CID: 618370

Max Phase: Preclinical

Molecular Formula: C15H14O4

Molecular Weight: 258.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ccc(=O)oc2c2c1OC(C)(C)C=C2

Standard InChI:  InChI=1S/C15H14O4/c1-15(2)7-6-10-13-9(4-5-12(16)18-13)8-11(17-3)14(10)19-15/h4-8H,1-3H3

Standard InChI Key:  UOFNVZWWIXXTMZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA529210

   Braylin

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: 258.27

Molecular Weight (Monoisotopic): 258.0892

AlogP: 2.99

#Rotatable Bonds: 1

Polar Surface Area: 48.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.74

Np Likeness Score: 2.28

References

1. Ito C, Itoigawa M, Otsuka T, Tokuda H, Nishino H, Furukawa H..  (2000)  Constituents of Boronia pinnata.,  63  (10): [PMID:11076549] [10.1021/np0000318]

2. Lin TT, Huang YY, Tang GH, Cheng ZB, Liu X, Luo HB, Yin S..  (2014)  Prenylated coumarins: natural phosphodiesterase-4 inhibitors from Toddalia asiatica.,  77  (4): [PMID:24597921] [10.1021/np401040d]

3. Singh S, Agarwal K, Iqbal H, Yadav P, Yadav D, Chanda D, Tandon S, Khan F, Gupta AK, Gupta A..  (2020)  Synthesis and evaluation of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one derivatives as vasorelaxing agents.,  30  (1): [PMID:31711783] [10.1016/j.bmcl.2019.126759]

4. Gonçalves GA, Spillere AR, das Neves GM, Kagami LP, von Poser GL, Canto RFS, Eifler-Lima V..  (2020)  Natural and synthetic coumarins as antileishmanial agents: A review.,  203  [PMID:32668302] [10.1016/j.ejmech.2020.112514]

5. Nainawat KS, Singh S, Agarwal K, Iqbal H, Rani P, Bhatt D, Khan S, Chanda D, Bawankule DU, Tandon S, Khan F, Kumar Gupta A, Gupta A..  (2023)  Synthesis of 6-alkoxy and 6-hydroxy-alkyl amine derivatives of braylin as vasorelaxing agents.,  89  [PMID:37149230] [10.1016/j.bmcl.2023.129311]

Source

Source(1):

• Scientific Literature