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

ID: ALA467744

PubChem CID: 54704070

Max Phase: Preclinical

Molecular Formula: C25H34O4

Molecular Weight: 398.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (7E,12E,18R,20Z)-Variabilin | CHEMBL467744|(7E,12E,18R,20Z)-Variabilin|BDBM50478639

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

Standard InChI:  InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h8,11,14-17,20,26H,5-7,9-10,12-13H2,1-4H3/b18-8+,19-11+,23-16-/t20-/m1/s1

Standard InChI Key:  HPVSJNGZYYDDMU-QULDNTQISA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.6973   -2.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -2.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5553   -2.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586   -2.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -2.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -2.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -2.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -2.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7285   -2.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425   -2.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1565   -2.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8704   -2.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5844   -2.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -2.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0086   -2.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952   -3.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886   -3.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -3.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722   -3.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3916   -3.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1971   -3.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6063   -2.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -2.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4282   -2.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2235   -1.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5358   -4.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  1 16  1  0
  7  8  1  0
  8  9  2  0
  4  5  2  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19  1  2  0
  9 10  1  0
  5 20  1  0
  2  3  1  0
  9 21  1  0
 10 11  1  0
 13 22  1  6
 15 23  1  0
  5  6  1  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 15  1  0
  6  7  1  0
 25 27  1  0
 13 14  1  0
 26 28  1  0
  3  4  1  0
 24 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA467744

   (7E,12E,18R,20Z)-Variabilin

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: 0.32

Np Likeness Score: 2.51

References

1. Wang N, Song J, Jang KH, Lee HS, Li X, Oh KB, Shin J..  (2008)  Sesterterpenoids from the sponge Sarcotragus sp.,  71  (4): [PMID:18341287] [10.1021/np0780147]

2. Choi K, Hong J, Lee CO, Kim DK, Sim CJ, Im KS, Jung JH..  (2004)  Cytotoxic furanosesterterpenes from a marine sponge Psammocinia sp.,  67  (7): [PMID:15270579] [10.1021/np049922w]

3. 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