(1S,3R,5R,6aS,7R,8R,101S)-7,8-dimethyl-7-(3-methylenepent-4-enyl)decahydro-1H-naphtho[1-c]furan-1,3,5-triyl triacetate

ID: ALA3586097

PubChem CID: 122180082

Max Phase: Preclinical

Molecular Formula: C26H38O7

Molecular Weight: 462.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=C)CC[C@]1(C)[C@H](C)CC[C@@]23C(C[C@H](OC(C)=O)C[C@@H]12)[C@@H](OC(C)=O)O[C@H]3OC(C)=O

Standard InChI:  InChI=1S/C26H38O7/c1-8-15(2)9-11-25(7)16(3)10-12-26-21(13-20(14-22(25)26)30-17(4)27)23(31-18(5)28)33-24(26)32-19(6)29/h8,16,20-24H,1-2,9-14H2,3-7H3/t16-,20+,21?,22+,23+,24-,25-,26-/m1/s1

Standard InChI Key:  CCKILWOWDZILRL-QCXZFGTDSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.9679   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976   -2.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3161   -3.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7739    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -0.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699    2.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739    0.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6508   -2.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3016   -2.4624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9899    4.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    2.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646   -2.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300   -2.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439   -1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078   -3.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9933    2.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    2.6885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    1.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4756    4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0354    5.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2164    3.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2233    5.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2892    1.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2826    0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3319    2.2685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  5  6  1  0
  5  7  1  0
  6 14  1  0
  8  7  1  0
  8 13  1  0
  8 12  1  0
 13  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 14  1  0
 15 14  1  0
 15 16  1  0
 13 17  1  0
 12 18  1  0
 18 19  1  0
 11 20  1  6
 15 21  1  6
 21 22  1  0
 22 23  1  0
 22 24  2  0
  5 25  1  6
  8 26  1  6
 12 27  1  1
 17 16  1  0
 17  1  1  6
 19 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  2  0
 25 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3586097

   ---

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: 462.58

Molecular Weight (Monoisotopic): 462.2618

AlogP: 4.70

#Rotatable Bonds: 7

Polar Surface Area: 88.13

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: 3.07

References

1. De Ford C, Calderón C, Sehgal P, Fedosova NU, Murillo R, Olesen C, Nissen P, Møller JV, Merfort I..  (2015)  Discovery of Tricyclic Clerodane Diterpenes as Sarco/Endoplasmic Reticulum Ca(2+)-ATPase Inhibitors and Structure-Activity Relationships.,  78  (6): [PMID:25993619] [10.1021/acs.jnatprod.5b00062]

Source

Source(1):

• Scientific Literature