jatamansin

ID: ALA457257

PubChem CID: 668081

Max Phase: Preclinical

Molecular Formula: C19H20O5

Molecular Weight: 328.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Jatamansin | Selinidin|Jatamansin|Xanthogalin|[(9R)-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-h]chromen-9-yl] (Z)-2-methylbut-2-enoate|Spectrum5_000398|BSPBio_003337|MLS002472947|SPECTRUM1504159|CHEMBL457257|SCHEMBL12062120|HMS2193F07|BDBM50069685|FS-7060|SDCCGMLS-0066791.P001|SMR001397055|BRD-K07212038-001-02-1

Canonical SMILES:  C/C=C(/C)C(=O)O[C@@H]1Cc2c(ccc3ccc(=O)oc23)OC1(C)C

Standard InChI:  InChI=1S/C19H20O5/c1-5-11(2)18(21)22-15-10-13-14(24-19(15,3)4)8-6-12-7-9-16(20)23-17(12)13/h5-9,15H,10H2,1-4H3/b11-5-/t15-/m1/s1

Standard InChI Key:  RRHCDWLSHIIIIT-NVWZYQMFSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -3.0085    1.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5648    2.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888    2.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    2.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    1.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    1.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    2.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352    2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704    0.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7283    0.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0039   -0.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -2.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -2.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -2.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0068   -2.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2  3  1  0
 12 15  2  0
  5  8  1  0
  2 16  1  0
  6 10  1  0
  2 17  1  0
  9  7  1  0
  3 18  1  1
  7  8  2  0
 18 19  1  0
  9 10  2  0
 19 20  1  0
  3  4  1  0
 19 21  2  0
  4  6  1  0
 20 22  2  0
  5  6  2  0
 20 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA457257

   JATAMANSIN

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: 328.36

Molecular Weight (Monoisotopic): 328.1311

AlogP: 3.38

#Rotatable Bonds: 2

Polar Surface Area: 65.74

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.48

Np Likeness Score: 2.61

References

1. Valencia-Islas N, Abbas H, Bye R, Toscano R, Mata R..  (2002)  Phytotoxic compounds from Prionosciadium watsoni.,  65  (6): [PMID:12088423] [10.1021/np010448t]

2. PubChem BioAssay data set, 

3. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

4. Li JL, Gao LX, Meng FW, Tang CL, Zhang RJ, Li JY, Luo C, Li J, Zhao WM..  (2015)  PTP1B inhibitors from stems of Angelica keiskei (Ashitaba).,  25  (10): [PMID:25891102] [10.1016/j.bmcl.2015.04.003]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays