tagitinin C

ID: ALA463060

PubChem CID: 11256548

Max Phase: Preclinical

Molecular Formula: C19H24O6

Molecular Weight: 348.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: tagitinin C | tagitinin C|CHEMBL463060|MEGxp0_000077|BDBM50433428|[(3aR,4R,6R,7E,10Z,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-2,9-dioxo-3a,4,5,11a-tetrahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

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

Standard InChI:  InChI=1S/C19H24O6/c1-10(2)17(21)25-15-9-19(5,23)7-6-13(20)11(3)8-14-16(15)12(4)18(22)24-14/h6-8,10,14-16,23H,4,9H2,1-3,5H3/b7-6+,11-8-/t14-,15-,16+,19+/m1/s1

Standard InChI Key:  DUQSSEQKLJQACA-FESGBCJUSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    4.6833   -6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6833   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3954   -7.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3954   -6.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8308   -5.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1206   -5.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3997   -5.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3954   -8.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695   -7.9010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -4.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8202   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1086   -6.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4947   -7.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2711   -7.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4253   -6.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7845   -8.1226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2131   -6.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -5.8667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -5.8458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5500   -5.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5594   -4.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2786   -3.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8498   -3.7883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9883   -4.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2881   -2.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  2  3  1  0
  5  8  1  0
 13  6  1  0
  6  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  7  8  1  0
 16 18  2  0
  3  4  2  0
 17 19  2  0
  3  9  1  0
 14 20  1  1
  4 14  1  0
 13 21  1  6
  2 10  2  0
  6 22  1  1
 22 23  1  0
  8 11  1  0
 23 24  1  0
  1  2  1  0
 23 25  2  0
  8 12  1  1
 24 26  1  0
 13 14  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463060

   TAGITININ C

Molecule Features

Natural Product: No

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: 348.40

Molecular Weight (Monoisotopic): 348.1573

AlogP: 1.88

#Rotatable Bonds: 2

Polar Surface Area: 89.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 2.58

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 3.05

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. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

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. Schomburg C, Schuehly W, Da Costa FB, Klempnauer KH, Schmidt TJ..  (2013)  Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships.,  63  [PMID:23501116] [10.1016/j.ejmech.2013.02.018]

5. 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