3-(4,8-dimethyl-10-(2,6,6-trimethylcyclohex-1-enyl)deca-3,7-dienyl)furan-2(5H)-one

ID: ALA525915

PubChem CID: 10714247

Max Phase: Preclinical

Molecular Formula: C25H38O2

Molecular Weight: 370.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CC/C(C)=C/CC/C(C)=C/CCC2=CCOC2=O)C(C)(C)CCC1

Standard InChI:  InChI=1S/C25H38O2/c1-19(11-7-13-22-16-18-27-24(22)26)9-6-10-20(2)14-15-23-21(3)12-8-17-25(23,4)5/h10-11,16H,6-9,12-15,17-18H2,1-5H3/b19-11+,20-10+

Standard InChI Key:  JNEMQZQEAUFPOT-CWGBCDKESA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
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   -4.4958   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838   -6.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -4.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5042   -6.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3792   -7.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3579   -6.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -5.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -6.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2139   -5.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -7.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -6.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150   -5.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9289   -6.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9277   -7.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -6.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0729   -5.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7868   -6.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8748   -7.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6815   -7.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0951   -6.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439   -6.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7152   -5.2575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  5  7  1  0
 13 15  1  0
  1  2  1  0
 15 16  1  0
  3  8  1  0
 16 17  1  0
  1  6  1  0
 17 18  2  0
  3  9  1  0
 17 19  1  0
  2  3  1  0
 18 20  1  0
  4 10  1  0
 20 21  1  0
  3  4  1  0
 21 22  1  0
 22 23  2  0
 10 11  1  0
  4  5  2  0
 11 12  1  0
  5  6  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 12 13  2  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA525915

   4-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethylcyclohexen-1-yl)deca-3,7-dienyl]-2H-furan-5-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: 370.58

Molecular Weight (Monoisotopic): 370.2872

AlogP: 7.23

#Rotatable Bonds: 9

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.39

CX Basic pKa: ┄

CX LogP: 7.17

CX LogD: 7.17

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: 2.74

References

1. Kirsch G, Köng GM, Wright AD, Kaminsky R..  (2000)  A new bioactive sesterterpene and antiplasmodial alkaloids from the marine sponge hyrtios cf. erecta.,  63  (6): [PMID:10869210] [10.1021/np990555b]

Source

Source(1):

• Scientific Literature