(1R,2R,4aS,5R)-1-(hydroxymethyl)-1,4a-dimethyl-6-methylene-5-(2-(4-nitrophenoxy)ethyl)decahydronaphthalen-2-ol

ID: ALA4469909

PubChem CID: 155534297

Max Phase: Preclinical

Molecular Formula: C22H31NO5

Molecular Weight: 389.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1CCC2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1CCOc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C22H31NO5/c1-15-4-9-19-21(2,12-10-20(25)22(19,3)14-24)18(15)11-13-28-17-7-5-16(6-8-17)23(26)27/h5-8,18-20,24-25H,1,4,9-14H2,2-3H3/t18-,19?,20-,21+,22+/m1/s1

Standard InChI Key:  ZEKSDKMIWAFQQH-FAEIBLRNSA-N

Molfile:  

 
     RDKit          2D

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    5.7410  -18.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365  -17.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9275  -18.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349  -16.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349  -17.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402  -16.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0454  -16.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0420  -17.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440  -17.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4540  -17.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4575  -16.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7510  -16.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0381  -15.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7533  -15.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278  -17.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1674  -16.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4622  -14.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3301  -19.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4645  -14.0023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1734  -13.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8781  -14.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5865  -13.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5893  -12.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8778  -12.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1723  -12.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2990  -12.3785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3002  -11.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0061  -12.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  6
 12 14  1  6
  5 15  1  6
 11 16  2  0
 14 17  1  0
  1 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
 23 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4469909

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 389.49

Molecular Weight (Monoisotopic): 389.2202

AlogP: 4.11

#Rotatable Bonds: 6

Polar Surface Area: 92.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: 1.36

References

1. Wang W, Wu Y, Chen X, Zhang P, Li H, Chen L..  (2019)  Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation of their anti-inflammatory activities.,  162  [PMID:30419492] [10.1016/j.ejmech.2018.11.002]

Source

Source(1):

• Scientific Literature