3R,5-dihydroxy-2,2,8,8-tetramethyl-6-(2-methylpropanoyl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one

ID: ALA4540475

PubChem CID: 155549715

Max Phase: Preclinical

Molecular Formula: C20H24O6

Molecular Weight: 360.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C(=O)c1c(O)c2c(c3c1OC(C)(C)C=C3)OC(C)(C)[C@@H](O)C2=O

Standard InChI:  InChI=1S/C20H24O6/c1-9(2)13(21)11-14(22)12-15(23)18(24)20(5,6)26-17(12)10-7-8-19(3,4)25-16(10)11/h7-9,18,22,24H,1-6H3/t18-/m0/s1

Standard InChI Key:  YJKFINKKXCMYDY-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   26.4844   -7.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9066   -8.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6995   -8.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5730   -9.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3902   -9.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9816   -8.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3902  -10.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0955  -10.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0955   -8.9932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8008   -9.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7992  -10.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5034  -10.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2097  -10.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5027  -11.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5025   -8.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2109   -9.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9106   -8.9935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1997   -7.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4938   -8.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9169  -10.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9159  -11.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6251  -10.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3323  -10.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6261   -9.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6831  -10.6328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0967  -11.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  5  7  1  0
  5  9  1  0
  7  8  1  0
  8 11  1  0
 10  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 16  1  0
 15 10  1  0
 12 14  1  0
 15 16  2  0
 15 19  1  0
 16 17  1  0
 17  2  1  0
  2 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
  7 25  1  6
  8 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540475

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.41

Molecular Weight (Monoisotopic): 360.1573

AlogP: 3.13

#Rotatable Bonds: 2

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.54

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.96

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: 2.85

References

1. Fobofou SA, Franke K, Porzel A, Brandt W, Wessjohann LA..  (2016)  Tricyclic Acylphloroglucinols from Hypericum lanceolatum and Regioselective Synthesis of Selancins A and B.,  79  (4): [PMID:26950610] [10.1021/acs.jnatprod.5b00673]

Source

Source(1):

• Scientific Literature