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

ID: ALA4539418

PubChem CID: 155549866

Max Phase: Preclinical

Molecular Formula: C21H26O6

Molecular Weight: 374.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H26O6/c1-7-10(2)14(22)12-15(23)13-16(24)19(25)21(5,6)27-18(13)11-8-9-20(3,4)26-17(11)12/h8-10,19,23,25H,7H2,1-6H3/t10-,19-/m0/s1

Standard InChI Key:  SBOSKCSYCGVWKT-OVWNDWIMSA-N

Molfile:  

 
     RDKit          2D

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    5.7657  -13.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879  -13.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808  -13.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543  -15.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715  -15.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2629  -14.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715  -15.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768  -16.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768  -14.5898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821  -15.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805  -15.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7847  -16.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910  -15.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7840  -17.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7839  -14.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922  -14.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919  -14.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810  -13.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7751  -13.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1982  -16.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1972  -17.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9064  -15.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6136  -16.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9074  -15.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9644  -16.2293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780  -17.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3218  -15.8216    0.0000 C   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  1
  7 25  1  6
  8 26  2  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539418

   ---

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: 374.43

Molecular Weight (Monoisotopic): 374.1729

AlogP: 3.52

#Rotatable Bonds: 3

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: 4.44

CX LogD: 4.41

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: 2.86

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