Rabdoumbrosanin

ID: ALA5287210

Max Phase: Preclinical

Molecular Formula: C20H28O3

Molecular Weight: 316.44

Names and Identifiers

Canonical SMILES:  C=C1C(=O)C2=C[C@H]1CCC(=O)[C@]1(C)CCCC(C)(C)[C@H]1C[C@H]2O

Standard InChI:  InChI=1S/C20H28O3/c1-12-13-6-7-17(22)20(4)9-5-8-19(2,3)16(20)11-15(21)14(10-13)18(12)23/h10,13,15-16,21H,1,5-9,11H2,2-4H3/t13-,15-,16-,20-/m1/s1

Standard InChI Key:  HPCCGLBGTJGBJM-KHTYJDQRSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.3887   -0.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3887   -0.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742   -1.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598   -0.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598   -0.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742    0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    1.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    1.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    1.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691   -0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691   -0.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453   -1.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -1.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555    0.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016   -0.7743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887    0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    2.0118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2072   -0.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598    0.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598   -1.7099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616   -2.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 10 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
  4 15  1  0
 14 16  1  6
 13 17  2  0
 17 10  1  0
 12 18  2  0
 11 19  2  0
 10 20  1  6
  7 21  2  0
  5 22  1  6
  4 23  1  1
  3 24  1  0
  3 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287210

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.44

Molecular Weight (Monoisotopic): 316.2038

AlogP: 3.61

#Rotatable Bonds: ┄

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: 3.29

References

1. Asakawa Y, Ludwiczuk A..  (2018)  Chemical Constituents of Bryophytes: Structures and Biological Activity.,  81  (3): [PMID:29019405] [10.1021/acs.jnatprod.6b01046]

Source

Source(1):

• Scientific Literature