4-((2aS,2a1R,5aS,6R,7R,8aR)-6-hydroxy-2a,5a,7-trimethyl-2-oxodecahydro-2H-naphtho[1,8-bc]furan-6-yl)butanoic acid

ID: ALA1077925

PubChem CID: 46883326

Max Phase: Preclinical

Molecular Formula: C18H28O5

Molecular Weight: 324.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]1(O)CCCC(=O)O

Standard InChI:  InChI=1S/C18H28O5/c1-11-10-12-14-16(2,15(21)23-12)7-5-8-17(14,3)18(11,22)9-4-6-13(19)20/h11-12,14,22H,4-10H2,1-3H3,(H,19,20)/t11-,12-,14+,16+,17+,18-/m1/s1

Standard InChI Key:  KRTAGCAAGRLSRQ-GCTGDKDVSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.4065  -21.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773  -22.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773  -23.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9903  -23.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9903  -21.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6990  -22.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7006  -23.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4080  -23.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1207  -23.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1232  -22.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1986  -24.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1771  -24.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7055  -25.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2688  -23.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6942  -23.9721    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1197  -23.9725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4030  -21.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1164  -20.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8333  -21.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5467  -20.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2636  -21.0743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5431  -19.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1197  -21.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8395  -21.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6933  -21.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10  1  1  0
  4 11  1  0
 11 12  1  0
  8 12  1  0
 11 13  2  0
  4 14  1  6
  7 15  1  6
  8 16  1  6
  2  3  1  0
  1 17  1  1
  2  5  1  0
 17 18  1  0
  3  4  1  0
 18 19  1  0
  4  7  1  0
 19 20  1  0
  6  5  1  0
 20 21  2  0
  6  7  1  0
 20 22  1  0
  6  1  1  0
  1 23  1  0
  7  8  1  0
 10 24  1  6
  8  9  1  0
  6 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1077925

   4-[(1R,4S,8S,9R,10R,12R)-9-hydroxy-4,8,10-trimethyl-3-oxo-2-oxatricyclo[6.3.1.04,12]dodecan-9-yl]butanoic acid

Molecule Features

Natural Product: Yes

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: 324.42

Molecular Weight (Monoisotopic): 324.1937

AlogP: 2.75

#Rotatable Bonds: 4

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.53

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: -0.18

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: 3.09

References

1. Rigano D, Aviello G, Bruno M, Formisano C, Rosselli S, Capasso R, Senatore F, Izzo AA, Borrelli F..  (2009)  Antispasmodic effects and structure-activity relationships of labdane diterpenoids from Marrubium globosum ssp. libanoticum.,  72  (8): [PMID:19650652] [10.1021/np9002756]

Source

Source(1):

• Scientific Literature