sodium 3,4-secoisopimar-4(18),7,15-trien-3-oic acid

ID: ALA2088293

PubChem CID: 70691188

Max Phase: Preclinical

Molecular Formula: C20H29NaO2

Molecular Weight: 302.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C[C@@]1(C)CC[C@H]2C(=CC[C@@H](C(=C)C)[C@]2(C)CCC(=O)[O-])C1.[Na+]

Standard InChI:  InChI=1S/C20H30O2.Na/c1-6-19(4)11-9-17-15(13-19)7-8-16(14(2)3)20(17,5)12-10-18(21)22;/h6-7,16-17H,1-2,8-13H2,3-5H3,(H,21,22);/q;+1/p-1/t16-,17-,19-,20-;/m0./s1

Standard InChI Key:  JKMGJBPIBGEAKS-SSKJIEBZSA-M

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.6250    2.1875    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.7833   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6407   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389   -0.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3535    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3641    1.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539    1.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0669    1.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -0.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    0.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6429   -0.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300    1.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972   -1.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2123   -0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4960   -2.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901    1.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792   -0.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  1
  6  7  1  0
  2 13  1  0
 13 14  1  0
  2  3  1  0
 14 15  1  0
 15 16  2  0
  2  6  1  0
 15 17  1  0
  3  4  1  0
  3 18  1  1
  4  5  1  0
 18 19  1  0
  6 11  1  0
 18 20  2  0
  7  8  1  0
  9 21  1  1
  8  9  1  0
  9 22  1  0
  9 10  1  0
 22 23  2  0
 10 11  1  0
  6 24  1  6
  5  7  2  0
M  CHG  2   1   1  17  -1
M  END

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: 302.46

Molecular Weight (Monoisotopic): 302.2246

AlogP: 5.37

#Rotatable Bonds: 5

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.98

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 2.42

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: 3.36

References

1. Di Sotto A, Carbone F, Hrelia P, Maffei F, Castelli F, Sarpietro MG, Mazzanti G..  (2012)  Anticlastogenic effect in human lymphocytes by the sodium salt of 3,4-secoisopimar-4(18),7,15-trien-3-oic acid.,  75  (7): [PMID:22698255] [10.1021/np3001893]

Source

Source(1):

• Scientific Literature