1beta,2alpha-epoxytagitinin C

ID: ALA516873

PubChem CID: 44566960

Max Phase: Preclinical

Molecular Formula: C19H24O7

Molecular Weight: 364.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1Beta,2Alpha-Epoxytagitinin C | 1beta,2alpha-epoxytagitinin C|CHEMBL516873|CHEBI:145103|BDBM50466115

Canonical SMILES:  C=C1C(=O)O[C@@H]2/C=C(/C)C(=O)[C@@H]3O[C@H]3[C@](C)(O)C[C@@H](OC(=O)C(C)C)[C@@H]12

Standard InChI:  InChI=1S/C19H24O7/c1-8(2)17(21)25-12-7-19(5,23)16-15(26-16)14(20)9(3)6-11-13(12)10(4)18(22)24-11/h6,8,11-13,15-16,23H,4,7H2,1-3,5H3/b9-6-/t11-,12-,13+,15+,16-,19-/m1/s1

Standard InChI Key:  RRILSSWTIAVLMG-OZUMSVRBSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   13.5167   -7.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3928   -5.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7803   -4.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9674   -4.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0830   -6.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6996   -7.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5500   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3750   -3.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1067   -4.7774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1056   -3.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8195   -3.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3906   -3.5408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5345   -3.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8184   -2.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5674   -5.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2330   -6.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8488   -7.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5638   -6.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3898   -6.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0125   -7.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8500   -5.5833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3183   -7.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9403   -5.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3646   -7.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3710   -6.9426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9025   -5.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2420   -4.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4227   -5.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250   -4.2542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1833   -6.1292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
 15 16  1  0
  1 16  1  0
  4  7  1  1
 15  2  1  0
  4  8  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  2  3  1  0
 16 20  1  1
  2  9  1  1
 15 21  1  6
  3  4  1  0
 18 22  2  0
  9 10  1  0
 19 23  2  0
  4 27  1  0
  6 24  1  0
 10 11  1  0
  5 25  2  0
 27 26  1  0
 28 27  1  0
 26 28  1  0
 26  5  1  0
 10 12  2  0
  5  6  1  0
 11 13  1  0
 27 29  1  6
  6  1  2  0
 26 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA516873

   1beta,2alpha-epoxytagitinin C

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: 364.39

Molecular Weight (Monoisotopic): 364.1522

AlogP: 1.09

#Rotatable Bonds: 2

Polar Surface Area: 102.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.87

CX Basic pKa: ┄

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 2.92

References

1. Gu JQ, Gills JJ, Park EJ, Mata-Greenwood E, Hawthorne ME, Axelrod F, Chavez PI, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD..  (2002)  Sesquiterpenoids from Tithonia diversifolia with potential cancer chemopreventive activity.,  65  (4): [PMID:11975495] [10.1021/np010545m]

2. Chibli LA, Schmidt TJ, Nonato MC, Calil FA, Da Costa FB..  (2018)  Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.,  157  [PMID:30145372] [10.1016/j.ejmech.2018.08.033]

Source

Source(1):

• Scientific Literature