5-butylidene-3-(2-((1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decahydronaphthalen-1-yl)vinyl)furan-2(5H)-one

ID: ALA206309

PubChem CID: 44411124

Max Phase: Preclinical

Molecular Formula: C24H34O4

Molecular Weight: 386.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1/C=C/C1=C/C(=C/CCC)OC1=O

Standard InChI:  InChI=1S/C24H34O4/c1-5-6-7-18-14-17(22(27)28-18)9-10-19-16(2)8-11-20-23(19,3)13-12-21(26)24(20,4)15-25/h7,9-10,14,19-21,25-26H,2,5-6,8,11-13,15H2,1,3-4H3/b10-9+,18-7-/t19-,20+,21-,23+,24+/m1/s1

Standard InChI Key:  KVBBPCNOYXBXDZ-GIMZINDFSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  1  0  0  0  0  0999 V2000
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    2.4875  -20.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995  -20.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995  -19.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115  -19.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126  -20.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6236  -20.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3382  -20.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3371  -19.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6215  -19.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193  -18.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327  -17.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305  -17.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960  -16.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7390  -15.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139  -15.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6612  -16.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7812  -16.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042  -18.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736  -20.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917  -21.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792  -21.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0515  -19.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733  -22.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272  -15.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7607  -14.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809  -14.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144  -13.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115  -21.4458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
  5 10  1  0
 14 18  2  0
  6  7  1  0
  5 19  1  6
  7  8  1  0
  2 20  1  6
  8  9  1  0
  9 10  1  0
  3 21  1  0
  5  6  1  0
  3 22  1  1
 10 11  1  6
  9 23  2  0
 21 24  1  0
 11 12  2  0
 16 25  2  0
  1  2  1  0
 25 26  1  0
 12 13  1  0
 26 27  1  0
 13 14  1  0
 27 28  1  0
  6 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA206309

   5-butylidene-3-(2-((1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decahydronaphthalen-1-yl)vinyl)furan-2(5H)-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: 386.53

Molecular Weight (Monoisotopic): 386.2457

AlogP: 4.45

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: 3.42

References

1. Dai GF, Xu HW, Wang JF, Liu FW, Liu HM..  (2006)  Studies on the novel alpha-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues.,  16  (10): [PMID:16504503] [10.1016/j.bmcl.2006.02.011]

Source

Source(1):

• Scientific Literature