Marrulactone

ID: ALA1080254

PubChem CID: 44254165

Max Phase: Preclinical

Molecular Formula: C18H26O4

Molecular Weight: 306.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Marrulactone | Marrulactone|CHEMBL1080254

Canonical SMILES:  C[C@@H]1C[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]12CCCC(=O)O2

Standard InChI:  InChI=1S/C18H26O4/c1-11-10-12-14-16(2,15(20)21-12)7-5-8-17(14,3)18(11)9-4-6-13(19)22-18/h11-12,14H,4-10H2,1-3H3/t11-,12-,14+,16+,17+,18-/m1/s1

Standard InChI Key:  AKCKRZRPYZPWJE-GCTGDKDVSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.9439  -22.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421  -21.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9519  -21.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666  -20.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5684  -20.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554  -21.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8103  -22.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8103  -23.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247  -23.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247  -22.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349  -22.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365  -23.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9453  -23.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595  -23.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6621  -22.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334  -24.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140  -24.4655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394  -25.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018  -24.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2301  -24.1132    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6586  -24.1136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7505  -20.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3797  -22.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0162  -21.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  1  0
  7 10  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 11 12  1  0
 11  1  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15  1  1  0
  9 16  1  0
 16 17  1  0
 13 17  1  0
 16 18  2  0
  9 19  1  6
 12 20  1  6
 13 21  1  6
  1  2  1  0
  3 22  2  0
  1  6  1  1
 15 23  1  6
  2  3  1  0
 11 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1080254

   MARRULACTONE

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: 306.40

Molecular Weight (Monoisotopic): 306.1831

AlogP: 3.23

#Rotatable Bonds: ┄

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 3.36

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