13,15-diepicyllenin A

ID: ALA1078070

PubChem CID: 46883140

Max Phase: Preclinical

Molecular Formula: C20H30O5

Molecular Weight: 350.46

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@@]12CC[C@]1(CO[C@@H](O)C1)O2

Standard InChI:  InChI=1S/C20H30O5/c1-12-9-13-15-17(2,16(22)24-13)5-4-6-18(15,3)20(12)8-7-19(25-20)10-14(21)23-11-19/h12-15,21H,4-11H2,1-3H3/t12-,13-,14-,15+,17+,18+,19+,20-/m1/s1

Standard InChI Key:  IACFKHAQKGTVTR-VUKVDKESSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    4.6837   -5.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4818   -6.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9310   -5.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4107   -4.7540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6399   -5.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -6.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -6.6998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122   -5.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949   -6.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -7.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -8.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -8.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -6.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -7.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -8.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8452   -8.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592   -8.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617   -7.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -9.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6139   -9.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397  -10.0229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -8.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1302   -8.9781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767   -6.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582   -8.9785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7571   -5.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9162   -6.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  1  1  0
  1  2  1  0
  6  7  1  0
  7  1  1  0
  1  8  1  1
  8  9  1  0
  6  9  1  1
 10 11  1  0
 10 13  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 14 15  1  0
 14  6  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
 12 19  1  0
 19 20  1  0
 16 20  1  0
 19 21  2  0
 12 22  1  6
 15 23  1  6
 18 24  1  6
 16 25  1  6
  2  3  1  0
  3 26  1  1
  3  4  1  0
 14 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1078070

   13,15-DIEPICYLLENIN A

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: 350.46

Molecular Weight (Monoisotopic): 350.2093

AlogP: 2.79

#Rotatable Bonds: ┄

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 3.70

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