3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-6H-benzo[c]chromen-6-one

ID: ALA4764217

PubChem CID: 7088092

Max Phase: Preclinical

Molecular Formula: C19H18O8

Molecular Weight: 374.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2c2ccccc12

Standard InChI:  InChI=1S/C19H18O8/c20-8-14-15(21)16(22)17(23)19(27-14)25-9-5-6-11-10-3-1-2-4-12(10)18(24)26-13(11)7-9/h1-7,14-17,19-23H,8H2/t14-,15-,16+,17-,19-/m1/s1

Standard InChI Key:  WNWBIUMUTUWNJA-OGJJZOIMSA-N

Molfile:  

 
     RDKit          2D

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    4.9809  -18.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794  -19.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951  -18.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271  -16.6790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047  -17.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2933  -18.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908  -18.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9032  -17.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146  -17.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6172  -16.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286  -15.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418  -15.5384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900  -17.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889  -18.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3969  -18.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3951  -16.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1038  -17.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1026  -18.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8088  -18.4903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5207  -18.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2272  -18.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8111  -16.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5148  -17.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2260  -16.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2348  -16.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5264  -15.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8181  -16.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
  6  1  1  1
  7  2  1  6
  8  3  1  1
  9  4  1  6
 11 12  1  0
 13 14  2  0
 14 15  1  0
 15 18  2  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 23  1  0
 20 21  2  0
 14  1  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764217

   3-{[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-YL]oxy}-6H-benzo[C]chromen-6-one

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: 374.35

Molecular Weight (Monoisotopic): 374.1002

AlogP: 0.12

#Rotatable Bonds: 3

Polar Surface Area: 129.59

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 0.35

CX LogD: 0.35

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: 1.29

References

1. Liu Q,Miao Y,Wang X,Lv G,Peng Y,Li K,Li M,Qiu L,Lin J.  (2020)  Structure-based virtual screening and biological evaluation of novel non-bisphosphonate farnesyl pyrophosphate synthase inhibitors.,  186  [PMID:31785819] [10.1016/j.ejmech.2019.111905]

Source

Source(1):

• Scientific Literature