Taichunin A

ID: ALA4442635

PubChem CID: 145720902

Max Phase: Preclinical

Molecular Formula: C19H24O4

Molecular Weight: 316.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C[C@]1(C)C=C2C(=O)O[C@@]34CCCC(C)(C)[C@@H]3C(=O)O[C@@]24CC1

Standard InChI:  InChI=1S/C19H24O4/c1-5-17(4)9-10-18-12(11-17)14(20)22-19(18)8-6-7-16(2,3)13(19)15(21)23-18/h5,11,13H,1,6-10H2,2-4H3/t13-,17-,18-,19-/m0/s1

Standard InChI Key:  BRMDWWCONUOABG-VKOGCVSHSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    7.4756   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0664   -2.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8929   -2.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037   -4.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263   -4.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150   -3.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263   -5.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3405   -5.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506   -5.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3405   -3.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -3.0240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5077   -3.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511   -4.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3873   -5.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2017   -4.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6604   -3.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3627   -4.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0678   -3.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3611   -2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -2.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7537   -5.5891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607   -2.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3062   -3.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580   -3.3318    0.0000 H   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
  5  7  1  0
  5 10  1  0
  7  8  1  0
  8  9  1  0
 13  9  1  6
 10 13  1  0
 16 11  1  1
 11 12  1  0
 10 12  1  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 16 17  1  0
 16 20  1  0
 17 18  2  0
 18  2  1  0
  2 19  1  0
 19 20  1  0
 15 21  2  0
 12 22  2  0
  3 23  2  0
 10 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4442635

   ---

Molecule Features

Natural Product: Yes

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: 316.40

Molecular Weight (Monoisotopic): 316.1675

AlogP: 3.32

#Rotatable Bonds: 1

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: 2.91

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