(R)-5,5',7-trihydroxy-4'-methoxy-2'H-spiro[chroman-3,1'-cyclobutabenzen]-4-one

ID: ALA4548307

PubChem CID: 155554249

Max Phase: Preclinical

Molecular Formula: C17H14O6

Molecular Weight: 314.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1O)[C@@]1(COc3cc(O)cc(O)c3C1=O)C2

Standard InChI:  InChI=1S/C17H14O6/c1-22-13-2-8-6-17(10(8)5-11(13)19)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:  UVAGPWQTXXDQIY-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   24.9039   -9.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8998  -10.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7248  -10.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7289   -9.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0438   -8.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0427   -9.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7575  -10.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7558   -8.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4711   -8.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4699   -9.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1828  -10.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9027   -8.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1852   -8.5223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1805  -11.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4366  -11.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1531  -10.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1502   -9.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4348   -9.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8631   -9.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8681  -11.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8694  -11.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3293   -8.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7592  -11.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
  2  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
  9 13  1  0
 10 11  1  0
 11  1  1  0
  1 12  1  0
 12 13  1  0
 11 14  2  0
  3 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  4  1  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
  5 22  1  0
  7 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548307

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

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: 2.16

References

1. 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