trigonostemone

ID: ALA1078766

PubChem CID: 14731300

Max Phase: Preclinical

Molecular Formula: C20H22O4

Molecular Weight: 326.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Trigonostemone | trigonostemone|CHEMBL1078766|BDBM50446569

Canonical SMILES:  COC1=Cc2c(cc(OC)c3cc(C)c(OC)cc23)C(C)(C)C1=O

Standard InChI:  InChI=1S/C20H22O4/c1-11-7-14-12(8-16(11)22-4)13-9-18(24-6)19(21)20(2,3)15(13)10-17(14)23-5/h7-10H,1-6H3

Standard InChI Key:  SVSYTLDPFSIEJY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -3.6377    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6389    0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250    0.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9268    2.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    1.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118    0.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    1.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032    2.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986    0.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926   -0.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732   -0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0582   -0.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626    0.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684   -1.6247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793   -2.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577   -0.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412    1.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448    0.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3512    2.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3526    0.4351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0656    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5075    2.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7963    3.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  6 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
  3  6  2  0
 12 15  1  0
  9  7  1  0
 15 16  1  0
  1  2  2  0
 13 17  2  0
  7  8  2  0
 14 18  1  0
  8  5  1  0
 14 19  1  0
  9 10  2  0
  1 20  1  0
  5  4  2  0
  2 21  1  0
  4  1  1  0
 21 22  1  0
  8 23  1  0
  2  3  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078766

   TRIGONOSTEMONE

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: 326.39

Molecular Weight (Monoisotopic): 326.1518

AlogP: 4.01

#Rotatable Bonds: 3

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: 1.61

References

1. Seephonkai P, Sangdee A, Bunchalee P, Pyne SG..  (2009)  Cytotoxic and antiplasmodial compounds from the roots of Strophioblachia fimbricalyx.,  72  (10): [PMID:19778068] [10.1021/np900352n]

2. de Sousa LR, Ramalho SD, Burger MC, Nebo L, Fernandes JB, da Silva MF, Iemma MR, Corrêa CJ, de Souza DH, Lima MI, Vieira PC..  (2014)  Isolation of arginase inhibitors from the bioactivity-guided fractionation of Byrsonima coccolobifolia leaves and stems.,  77  (2): [PMID:24521209] [10.1021/np400717m]

Source

Source(1):

• Scientific Literature