13-epicyllenin A

ID: ALA1078069

PubChem CID: 44254085

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-DEEWQJAJSA-N

Molfile:  

     RDKit          2D

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   -1.2573   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080   -5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284   -4.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0991   -4.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8913   -6.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957   -6.6074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -5.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -6.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0281   -7.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0281   -8.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139   -8.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139   -6.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6039   -7.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6022   -8.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8937   -8.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799   -8.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1053   -9.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -9.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5992   -9.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0365   -8.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088   -8.8857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623   -6.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808   -8.8861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -5.2592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8226   -6.4379    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
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  8  9  1  0
  6  9  1  1
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 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  6
  3  4  1  0
 14 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1078069

   13-EPICYLLENIN 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