isomuscomosin

ID: ALA3594097

PubChem CID: 122182400

Max Phase: Preclinical

Molecular Formula: C17H14O6

Molecular Weight: 314.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1O)C[C@]21COc2cc(O)cc(O)c2C1=O

Standard InChI:  InChI=1S/C17H14O6/c1-22-13-5-10-8(2-11(13)19)6-17(10)7-23-14-4-9(18)3-12(20)15(14)16(17)21/h2-5,18-20H,6-7H2,1H3/t17-/m0/s1

Standard InChI Key:  CIUPXTYTXDYKRQ-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -5.2012    1.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5921    2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928    2.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006    1.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    2.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -0.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8904    3.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -0.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    3.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6594    1.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0352    2.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4933    2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5606    1.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1698    0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7116    0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7198    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2228   -0.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9042   -1.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
  2 16  1  0
 15  1  1  0
  3  4  2  0
  4  5  1  0
  5  8  2  0
  7  6  2  0
  6  3  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9  1  1  0
  1 10  1  0
 10 11  1  0
  9 12  2  0
  3 13  1  0
  5 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 19 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3594097

   ---

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: 314.29

Molecular Weight (Monoisotopic): 314.0790

AlogP: 1.88

#Rotatable Bonds: 1

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: 2.59

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: 2.13

References

1. Alali F, El-Elimat T, Albataineh H, Al-Balas Q, Al-Gharaibeh M, Falkinham JO, Chen WL, Swanson SM, Oberlies NH..  (2015)  Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii.,  78  (7): [PMID:26147490] [10.1021/acs.jnatprod.5b00357]

2. Schwikkard S, Whitmore H, Sishtla K, Sulaiman RS, Shetty T, Basavarajappa HD, Waller C, Alqahtani A, Frankemoelle L, Chapman A, Crouch N, Wetschnig W, Knirsch W, Andriantiana J, Mas-Claret E, Langat MK, Mulholland D, Corson TW..  (2019)  The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae ( sensu APGII).,  82  (5): [PMID:30951308] [10.1021/acs.jnatprod.8b00989]

Source

Source(1):

• Scientific Literature