rac-jungermannenone C

ID: ALA4175099

PubChem CID: 85431953

Max Phase: Preclinical

Molecular Formula: C20H28O2

Molecular Weight: 300.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)C2C3=C(CCC4C(C)(C)CCCC34C)CC1C2O

Standard InChI:  InChI=1S/C20H28O2/c1-11-13-10-12-6-7-14-19(2,3)8-5-9-20(14,4)16(12)15(17(11)21)18(13)22/h13-15,18,22H,1,5-10H2,2-4H3

Standard InChI Key:  FQDAEGYLRVQRKN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    4.1111   -6.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085   -6.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -6.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -4.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -5.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140   -4.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4158   -4.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -5.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -6.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124   -5.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139   -4.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8118   -4.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5177   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268   -3.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8289   -3.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1178   -3.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4048   -4.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275   -2.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8119   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -2.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8266   -2.4282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  8  2  1  0
  7  6  1  0
  8  7  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  2  0
 16 11  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
  7 17  1  0
 16 18  1  0
 14 19  1  0
 18 19  1  0
 19 20  2  0
 18 21  2  0
 15 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175099

   16-Hydroxy-3,7,7-trimethyl-14-methylidenetetracyclo[11.2.1.02,11.03,8]hexadec-2(11)-en-15-one

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: 300.44

Molecular Weight (Monoisotopic): 300.2089

AlogP: 4.05

#Rotatable Bonds: ┄

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.54

Np Likeness Score: 3.08

References

1. Yue Z, Xiao X, Wu J, Zhou X, Liu W, Liu Y, Li H, Chen G, Wu Y, Lei X..  (2018)  ent-Jungermannenone C Triggers Reactive Oxygen Species-Dependent Cell Differentiation in Leukemia Cells.,  81  (2): [PMID:29394050] [10.1021/acs.jnatprod.7b00722]

Source

Source(1):

• Scientific Literature