(16S*)-(9alpha-16alpha),(15-16alpha)-diepoxy-13beta,14beta-dihydroxy-15R-ethoxylabdan-6beta(19)-olide

ID: ALA1080253

PubChem CID: 44254084

Max Phase: Preclinical

Molecular Formula: C22H34O7

Molecular Weight: 410.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Marrulibacetal | Marrulibacetal|CHEMBL1080253

Canonical SMILES:  CCO[C@@H]1O[C@@H]2O[C@]3(CC[C@]2(O)[C@H]1O)[C@H](C)C[C@H]1OC(=O)[C@@]2(C)CCC[C@@]3(C)[C@@H]12

Standard InChI:  InChI=1S/C22H34O7/c1-5-26-16-15(23)21(25)9-10-22(29-18(21)28-16)12(2)11-13-14-19(3,17(24)27-13)7-6-8-20(14,22)4/h12-16,18,23,25H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,18-,19+,20+,21+,22-/m1/s1

Standard InChI Key:  ROLCCWPTXCTWNC-PQWYHOPNSA-N

Molfile:  

     RDKit          2D

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   12.3299  -14.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1274  -14.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9547  -12.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7419  -13.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1982  -14.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1982  -15.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9120  -15.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9120  -14.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6215  -14.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6231  -15.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3313  -15.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0448  -15.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0474  -14.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1205  -16.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1001  -16.6982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6269  -17.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1897  -16.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6167  -16.3462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7620  -14.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0439  -16.3466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7522  -12.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3383  -13.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0717  -12.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9388  -12.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1233  -11.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1629  -12.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7444  -11.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5205  -11.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3201  -11.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9019  -11.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9207  -13.8497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2026  -13.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  1  1  0
  7 14  1  0
 14 15  1  0
 11 15  1  0
 14 16  2  0
  7 17  1  6
 10 18  1  6
 13 19  1  6
  2 22  1  0
 11 20  1  6
 21 22  1  0
 21  3  1  0
  3  4  1  0
  1  2  1  0
  1  4  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
  5  6  1  0
 21 26  1  1
  5  8  1  0
 25 27  1  1
  6  7  1  0
 24 28  1  6
  7 10  1  0
 28 29  1  0
  9  8  1  0
 29 30  1  0
  9 10  1  0
 22 31  1  1
  9  1  1  0
  9 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1080253

   MARRULIBACETAL

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: 410.51

Molecular Weight (Monoisotopic): 410.2305

AlogP: 2.12

#Rotatable Bonds: 2

Polar Surface Area: 94.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.77

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: 3.33

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