bavachinin

ID: ALA458053

PubChem CID: 44584224

Max Phase: Preclinical

Molecular Formula: C21H20O4

Molecular Weight: 336.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bavachinin | CHEMBL458053|BDBM50084041

Canonical SMILES:  COc1cc2oc(-c3ccc(O)cc3)cc(=O)c2cc1CC=C(C)C

Standard InChI:  InChI=1S/C21H20O4/c1-13(2)4-5-15-10-17-18(23)11-20(14-6-8-16(22)9-7-14)25-21(17)12-19(15)24-3/h4,6-12,22H,5H2,1-3H3

Standard InChI Key:  BVTZAHKRSBADDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.8486  -10.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8474  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622  -12.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5604  -10.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758  -10.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2746  -11.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9915  -12.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7142  -11.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7154  -10.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9939  -10.4244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9892  -12.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4291  -10.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1429  -10.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8579  -10.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8603   -9.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1418   -9.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4298   -9.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1326  -12.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185  -11.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037  -12.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9895  -11.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030  -12.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1340  -10.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1338   -9.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5753   -9.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  5 10  1  0
  2 18  1  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
 19 20  2  0
  8  9  2  0
 20 21  1  0
  9 10  1  0
 20 22  1  0
  5  6  1  0
  1 23  1  0
  7 11  2  0
 23 24  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA458053

   BAVACHININ

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: 336.39

Molecular Weight (Monoisotopic): 336.1362

AlogP: 4.68

#Rotatable Bonds: 4

Polar Surface Area: 59.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: 1.27

References

1. Lale A, Herbert JM, Augereau JM, Billon M, Leconte M, Gleye J..  (1996)  Ability of different flavonoids to inhibit the procoagulant activity of adherent human monocytes.,  59  (3): [PMID:8882428] [10.1021/np960057s]

2. Du G, Feng L, Yang Z, Shi J, Huang C, Guo F, Li B, Zhu W, Li Y..  (2015)  Separation and peroxisome proliferator-activated receptor-γ agonist activity evaluation of synthetic racemic bavachinin enantiomers.,  25  (12): [PMID:25978962] [10.1016/j.bmcl.2015.04.029]

3. Won TH, Song IH, Kim KH, Yang WY, Lee SK, Oh DC, Oh WK, Oh KB, Shin J..  (2015)  Bioactive Metabolites from the Fruits of Psoralea corylifolia.,  78  (4): [PMID:25710081] [10.1021/np500834d]

Source

Source(1):

• Scientific Literature