Taichunin D

ID: ALA4457649

PubChem CID: 155525805

Max Phase: Preclinical

Molecular Formula: C19H22O3

Molecular Weight: 298.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C[C@]1(C)CC2=C(O)C(=O)C3=C(CCCC3(C)C)C2=CC1=O

Standard InChI:  InChI=1S/C19H22O3/c1-5-19(4)10-13-12(9-14(19)20)11-7-6-8-18(2,3)15(11)17(22)16(13)21/h5,9,21H,1,6-8,10H2,2-4H3/t19-/m1/s1

Standard InChI Key:  KQPLUKSSTZDQCK-LJQANCHMSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   17.2518   -2.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8432   -2.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6644   -2.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3916   -5.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9872   -5.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5741   -5.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2814   -3.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2814   -4.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9908   -3.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7002   -3.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6968   -4.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4029   -5.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1171   -4.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4099   -3.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1206   -3.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8325   -3.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1375   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4152   -2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3983   -6.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8225   -5.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1475   -1.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0811   -3.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  7  9  1  0
  8  5  1  0
  5 11  1  0
 10  9  1  0
 10 11  2  0
 10 14  1  0
 11 12  1  0
 12 13  1  0
 13 15  2  0
 14 15  1  0
 14 18  2  0
 15 16  1  0
 16  2  1  0
  2 17  1  0
 17 18  1  0
 12 19  2  0
 13 20  1  0
 17 21  2  0
  3 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4457649

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 298.38

Molecular Weight (Monoisotopic): 298.1569

AlogP: 3.98

#Rotatable Bonds: 1

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: 9.53

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: 3.58

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: 2.08

References

1. Kato H, Sebe M, Nagaki M, Eguchi K, Kagiyama I, Hitora Y, Frisvad JC, Williams RM, Tsukamoto S..  (2019)  Taichunins A-D, Norditerpenes from Aspergillus taichungensis (IBT 19404).,  82  (5): [PMID:30995043] [10.1021/acs.jnatprod.8b01032]

Source

Source(1):

• Scientific Literature