tagitinin A

ID: ALA518700

Cas Number: 59979-61-2

PubChem CID: 181254

Product Number: T614305, Order Now?

Max Phase: Preclinical

Molecular Formula: C19H28O7

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C[C@H](C)[C@@]3(O)C[C@H](O)[C@@](C)(C[C@@H](OC(=O)C(C)C)[C@@H]12)O3

Standard InChI:  InChI=1S/C19H28O7/c1-9(2)16(21)25-13-7-18(5)14(20)8-19(23,26-18)10(3)6-12-15(13)11(4)17(22)24-12/h9-10,12-15,20,23H,4,6-8H2,1-3,5H3/t10-,12+,13+,14-,15-,18+,19+/m0/s1

Standard InChI Key:  HREHFPZHVCNOMQ-XNNFIIJVSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    0.9273   -5.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4467   -5.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -5.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2773   -3.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8204   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1495   -4.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063   -4.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -3.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -2.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7062   -2.1543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2773   -2.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2773   -1.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -2.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275   -4.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -4.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3138   -5.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0283   -6.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -5.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229   -2.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3991   -4.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4301   -4.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120   -2.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7635   -2.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335   -4.1961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -6.0416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  2  9  1  0
  9 10  1  0
  8 10  1  0
  6 11  1  1
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  5 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
  4 21  1  0
  8 22  1  0
  2  1  1  6
  9 23  1  0
 23 22  1  0
  2  3  1  0
  9 24  1  6
  3  4  1  0
  8 25  1  6
  4  5  1  0
 22 26  1  6
  5  6  1  0
  5 27  1  6
  6  7  1  0
  4 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA518700

   tagitinin A

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: 368.43

Molecular Weight (Monoisotopic): 368.1835

AlogP: 1.31

#Rotatable Bonds: 2

Polar Surface Area: 102.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.75

CX Basic pKa: ┄

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: 3.19

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. Lin HR..  (2012)  Sesquiterpene lactones from Tithonia diversifolia act as peroxisome proliferator-activated receptor agonists.,  22  (8): [PMID:22424975] [10.1016/j.bmcl.2012.02.043]

3. Lin H.  (2013)  Identification of liver X receptor and farnesoid X receptor dual agonists from Tithonia diversifolia,  22  (7): [10.1007/s00044-012-0359-5]

4. 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