5-ethylidene-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: ALA205153

PubChem CID: 44411108

Max Phase: Preclinical

Molecular Formula: C22H30O4

Molecular Weight: 358.48

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/C)OC1=O

Standard InChI:  InChI=1S/C22H30O4/c1-5-16-12-15(20(25)26-16)7-8-17-14(2)6-9-18-21(17,3)11-10-19(24)22(18,4)13-23/h5,7-8,12,17-19,23-24H,2,6,9-11,13H2,1,3-4H3/b8-7+,16-5-/t17-,18+,19-,21+,22+/m1/s1

Standard InChI Key:  ZIEKMMQLKMDFSM-UTPJPTOUSA-N

Molfile:  

     RDKit          2D

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    8.5417  -10.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2537  -11.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2537   -9.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9657   -9.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9668  -10.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6778  -11.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3924  -10.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3913   -9.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6757   -9.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6735   -8.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3869   -8.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3847   -7.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0502   -6.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7932   -6.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9681   -6.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7154   -6.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8353   -7.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9583   -8.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8278  -11.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2458  -11.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5333  -11.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1057   -9.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5275  -12.2723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4813   -5.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8148   -4.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9657  -11.6333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  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
  6 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA205153

   (5Z)-3-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-5-ethylidenefuran-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: 358.48

Molecular Weight (Monoisotopic): 358.2144

AlogP: 3.67

#Rotatable Bonds: 3

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: 2.98

CX LogD: 2.98

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: 3.34

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