Taichunin B

ID: ALA4459561

PubChem CID: 145720903

Max Phase: Preclinical

Molecular Formula: C19H26O5

Molecular Weight: 334.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C[C@@]1(C)CCC2=C(C(=O)O[C@]23CCCC(C)(C)[C@@H]3C(=O)O)[C@@H]1O

Standard InChI:  InChI=1S/C19H26O5/c1-5-18(4)10-7-11-12(14(18)20)16(23)24-19(11)9-6-8-17(2,3)13(19)15(21)22/h5,13-14,20H,1,6-10H2,2-4H3,(H,21,22)/t13-,14-,18-,19+/m0/s1

Standard InChI Key:  QQXHZJNYZQQVRZ-KODHJQJWSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.4797   -7.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705   -8.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8970   -8.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901   -8.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443   -9.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -8.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4159   -9.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091  -10.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218  -10.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5659   -9.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0552   -9.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3914  -10.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2058  -10.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -9.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668   -9.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0719   -9.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3652   -7.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6590   -8.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578  -10.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3103   -9.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5606   -8.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -7.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8503   -7.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7796   -9.5375    0.0000 O   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
 11  9  1  6
 10 11  1  0
 14 11  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 15  2  0
 14 18  1  0
 15 16  1  0
 16  2  1  0
  2 17  1  0
 17 18  1  0
 13 19  2  0
  3 20  2  0
 10 21  1  6
 21 22  1  0
 21 23  2  0
 16 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4459561

   ---

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: 334.41

Molecular Weight (Monoisotopic): 334.1780

AlogP: 2.84

#Rotatable Bonds: 2

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.41

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 0.06

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.60

Np Likeness Score: 2.45

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