(Z)-5-((R,5Z,10Z)-13-(furan-3-yl)-2,6,11-trimethyltrideca-5,10-dienylidene)-4-hydroxy-3-methylfuran-2(5H)-one

ID: ALA574762

PubChem CID: 54736252

Max Phase: Preclinical

Molecular Formula: C25H34O4

Molecular Weight: 398.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(O)/C(=C/[C@H](C)CC/C=C(/C)CCC/C=C(/C)CCc2ccoc2)OC1=O

Standard InChI:  InChI=1S/C25H34O4/c1-18(8-5-6-9-19(2)12-13-22-14-15-28-17-22)10-7-11-20(3)16-23-24(26)21(4)25(27)29-23/h9-10,14-17,20,26H,5-8,11-13H2,1-4H3/b18-10-,19-9-,23-16-/t20-/m1/s1

Standard InChI Key:  KLKIESMJEUHQLI-KLURGBKRSA-N

Molfile:  

     RDKit          2D

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    0.0709  -16.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7849  -15.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6028  -19.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063  -20.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019  -20.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583  -21.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042  -21.1047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230  -19.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468  -15.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3600  -16.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0
 13 20  1  6
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  2  3  1  0
 10 11  1  0
  5  6  1  0
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 23 24  2  0
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  1  2  1  0
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 12 13  1  0
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  6  7  1  0
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  3  4  1  0
  4 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA574762

   (5Z)-5-[(2R,5Z,10Z)-13-(furan-3-yl)-2,6,11-trimethyltrideca-5,10-dienylidene]-4-hydroxy-3-methylfuran-2-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: 398.54

Molecular Weight (Monoisotopic): 398.2457

AlogP: 6.96

#Rotatable Bonds: 11

Polar Surface Area: 59.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.07

CX Basic pKa: ┄

CX LogP: 6.53

CX LogD: 6.03

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: 2.40

References

1. 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