(S)-3,5a,9-[trimethyl-2-oxo-2,4,5,5a,6,7-hexahydronaphtho[1,2-b]furan-8-yl]acetate

ID: ALA4089397

Cas Number: 6308-44-7

PubChem CID: 237944

Max Phase: Preclinical

Molecular Formula: C17H20O4

Molecular Weight: 288.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC1=C(C)C2=C3OC(=O)C(C)=C3CC[C@@]2(C)CC1

Standard InChI:  InChI=1S/C17H20O4/c1-9-12-5-7-17(4)8-6-13(20-11(3)18)10(2)14(17)15(12)21-16(9)19/h5-8H2,1-4H3/t17-/m0/s1

Standard InChI Key:  UVZIWNWWHZPYGX-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   18.4253   -8.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7077   -8.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9942   -8.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9942   -9.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2828   -9.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5649   -9.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5649   -8.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2828   -8.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8474   -9.8755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7158   -9.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4253   -9.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0322  -10.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7020  -10.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8864  -10.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1192  -11.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8433   -9.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2845  -10.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9874   -7.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1350   -9.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4220   -9.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1357   -8.6404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  6  5  2  0
  7  6  1  0
  8  7  1  0
  3  8  1  0
  6  9  1  0
  4 10  2  0
 11 10  1  0
 11  1  1  0
 11 12  2  0
 13 12  1  0
 14 13  1  0
 10 14  1  0
 13 15  2  0
 12 16  1  0
  5 17  1  0
  3 18  1  1
  9 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089397

   Eudesmatrienolide, acetate

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: 288.34

Molecular Weight (Monoisotopic): 288.1362

AlogP: 3.54

#Rotatable Bonds: 1

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.98

CX LogD: 1.98

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 1.90

References

1. Chinthakindi PK, Singh J, Gupta S, Nargotra A, Mahajan P, Kaul A, Ahmed Z, Koul S, Sangwan PL..  (2017)  Synthesis of α-santonin derivatives for diminutive effect on T and B-cell proliferation and their structure activity relationships.,  127  [PMID:27847171] [10.1016/j.ejmech.2016.11.018]

Source

Source(1):

• Scientific Literature