(3''R,4''S)-2',4',6'-trihydroxy-3'-(4-isopropyl-1-methylcyclohex-1-en-3-yl)-dihydrochalcone

ID: ALA458842

PubChem CID: 14078583

Max Phase: Preclinical

Molecular Formula: C25H30O4

Molecular Weight: 394.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C[C@H](c2c(O)cc(O)c(C(=O)CCc3ccccc3)c2O)[C@H](C(C)C)CC1

Standard InChI:  InChI=1S/C25H30O4/c1-15(2)18-11-9-16(3)13-19(18)23-21(27)14-22(28)24(25(23)29)20(26)12-10-17-7-5-4-6-8-17/h4-8,13-15,18-19,27-29H,9-12H2,1-3H3/t18-,19-/m0/s1

Standard InChI Key:  GHISAUFWVUOBIR-OALUTQOASA-N

Molfile:  

     RDKit          2D

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    9.2902   -0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2891   -1.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0039   -2.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7203   -1.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7175   -0.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0021   -0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0020    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7170    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7166    1.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0027    1.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2876    1.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2864    0.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5757   -0.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0037   -2.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4304   -0.5020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4355   -2.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4367   -2.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1493   -1.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8644   -2.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5782   -1.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2920   -2.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0054   -1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0045   -0.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2844   -0.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5740   -0.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4318    0.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5733    1.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1417   -0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 14  1  0
  1  2  2  0
  5 15  1  0
  3  4  2  0
  4 16  1  0
 16 17  2  0
  4  5  1  0
 16 18  1  0
  2  3  1  0
 18 19  1  0
  5  6  2  0
 19 20  1  0
  7 12  1  0
 20 21  2  0
  8  9  1  0
 21 22  1  0
  9 10  1  0
 22 23  2  0
 10 11  1  0
 23 24  1  0
 11 12  2  0
 24 25  2  0
 25 20  1  0
  7  6  1  1
  8 26  1  1
  6  1  1  0
 11 27  1  0
  1 13  1  0
 26 28  1  0
  7  8  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA458842

   LINDERATIN

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: 394.51

Molecular Weight (Monoisotopic): 394.2144

AlogP: 5.71

#Rotatable Bonds: 6

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.76

CX Basic pKa: ┄

CX LogP: 7.21

CX LogD: 7.06

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 1.75

References

1. Benosman A, Oger J, Richomme P, Bruneton J, Roussakis C, Ito K, Ichino K, Hamid A. Hadi A.  (1997)  New Terpenylated Dihydrochalcone Derivatives Isolated from Mitrella kentii ,  60  (9): [10.1021/np9700331]

Source

Source(1):

• Scientific Literature