4-Hydroxy-9-deoxoidiadione

ID: ALA501069

PubChem CID: 11349694

Max Phase: Preclinical

Molecular Formula: C25H38O3

Molecular Weight: 386.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\CC/C(C)=C/C[C@H](O)c1ccoc1)CC/C=C(\C)CC(=O)CC(C)C

Standard InChI:  InChI=1S/C25H38O3/c1-19(2)16-24(26)17-22(5)11-7-9-20(3)8-6-10-21(4)12-13-25(27)23-14-15-28-18-23/h8,11-12,14-15,18-19,25,27H,6-7,9-10,13,16-17H2,1-5H3/b20-8+,21-12+,22-11+/t25-/m0/s1

Standard InChI Key:  UZXKOVIRYVHQGU-PGMCJAAPSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -2.2296    0.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156    1.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    0.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877    1.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403    1.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682    1.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    0.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1962    1.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102    0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6241    1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381    0.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0521    1.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7661    0.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4800    1.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2341    0.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7853    1.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3720    2.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5653    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7679    0.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6223    2.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664    2.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895    2.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5174    2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 14 15  1  0
  7  8  1  0
 15 16  1  0
 16 17  1  0
  8  9  2  0
  4  5  2  0
  9 10  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
  2  3  1  0
 15 21  1  1
 10 11  1  0
 12 22  1  0
  5  6  1  0
  8 23  1  0
 11 12  1  0
  4 24  1  0
  1  2  1  0
  2 25  2  0
 12 13  2  0
  1 26  1  0
  6  7  1  0
 26 27  1  0
 13 14  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA501069

   (6E,10E,14E,17S)-17-(furan-3-yl)-17-hydroxy-2,6,10,14-tetramethylheptadeca-6,10,14-trien-4-one

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: 386.58

Molecular Weight (Monoisotopic): 386.2821

AlogP: 7.11

#Rotatable Bonds: 13

Polar Surface Area: 50.44

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.97

CX Basic pKa: ┄

CX LogP: 6.26

CX LogD: 6.26

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: 1.92

References

1. Rho JR, Lee HS, Shin HJ, Ahn JW, Kim JY, Sim CJ, Shin J..  (2004)  New sesterterpenes from the sponge Smenospongia sp.,  67  (10): [PMID:15497955] [10.1021/np040103l]

2. Song J, Jeong W, Wang N, Lee HS, Sim CJ, Oh KB, Shin J..  (2008)  Scalarane sesterterpenes from the sponge Smenospongia sp.,  71  (11): [PMID:18973387] [10.1021/np8003694]

Source

Source(1):

• Scientific Literature