(1R,3S,5S,5aS,7S,9R,9aS,9bR)-5-hydroxy-1,3-dimethoxy-7,9a-dimethyl-6-methylene-1,3,5,5a,6,7,8,9,9a,9b-decahydronaphtho[2,1-c]furan-9-yl 3-phenylpropanoate

ID: ALA2252774

PubChem CID: 11704895

Max Phase: Preclinical

Molecular Formula: C26H34O6

Molecular Weight: 442.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@@H]2[C@@H](O)C=C3[C@@H](OC)O[C@@H](OC)[C@@H]3[C@@]2(C)[C@H](OC(=O)CCc2ccccc2)C[C@@H]1C

Standard InChI:  InChI=1S/C26H34O6/c1-15-13-20(31-21(28)12-11-17-9-7-6-8-10-17)26(3)22(16(15)2)19(27)14-18-23(26)25(30-5)32-24(18)29-4/h6-10,14-15,19-20,22-25,27H,2,11-13H2,1,3-5H3/t15-,19-,20+,22+,23+,24-,25+,26-/m0/s1

Standard InChI Key:  RHYMAECQOXIJAK-WWRMZXHISA-N

Molfile:  

     RDKit          2D

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   16.6410  -12.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5306  -15.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9430  -12.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.5331   -8.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8231   -8.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8262   -9.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3516  -13.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0620  -13.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6695  -13.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3345  -12.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5201  -12.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9718  -11.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2225  -11.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4692  -13.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7235  -14.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3536  -15.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  1  0
  7  8  1  0
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  4 11  1  1
  3 12  2  0
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 20 21  1  0
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 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 27  1  0
 27 28  1  6
 28 29  1  0
 25 30  1  6
 30 31  1  0
  7 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2252774

   [(1R,3S,5S,5aS,7S,9R,9aS,9bR)-5-hydroxy-1,3-dimethoxy-7,9a-dimethyl-6-methylidene-1,3,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9-yl] 3-phenylpropanoate

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: 442.55

Molecular Weight (Monoisotopic): 442.2355

AlogP: 3.64

#Rotatable Bonds: 6

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: 2.14

References

1. Brennan NJ, Larsen L, Lorimer SD, Perry NB, Chapin EL, Werk TL, Henry MJ, Hahn DR..  (2006)  Fungicidal sesquiterpene dialdehyde cinnamates from Pseudowintera axillaris.,  54  (2): [PMID:16417306] [10.1021/jf052585s]

Source

Source(1):

• Scientific Literature