4-methyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-8,9,10,11-tetrahydrocyclohepta[c]chromen-6(7H)-one

ID: ALA4794885

PubChem CID: 7092946

Max Phase: Preclinical

Molecular Formula: C21H26O8

Molecular Weight: 406.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)ccc2c3c(c(=O)oc12)CCCCC3

Standard InChI:  InChI=1S/C21H26O8/c1-10-14(27-21-18(25)17(24)16(23)15(9-22)28-21)8-7-12-11-5-3-2-4-6-13(11)20(26)29-19(10)12/h7-8,15-18,21-25H,2-6,9H2,1H3/t15-,16-,17+,18-,21-/m1/s1

Standard InChI Key:  XMAZBNRXXKJBCE-ZIKOTGLESA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    5.3812  -11.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9797  -11.7468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5954  -10.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6274   -9.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -9.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937  -10.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9911  -10.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035  -10.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150   -9.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -9.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289   -8.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7422   -8.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904   -9.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0892  -10.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7973  -11.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7955   -9.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5041   -9.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5029  -10.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2091  -11.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9210  -10.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6276  -11.0070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7989  -11.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9193   -9.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2115   -9.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0922   -8.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6908   -9.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6532   -7.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9382   -8.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4743   -8.0090    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 24  1  0
 18 19  1  0
 19 20  1  0
 20 23  1  0
 20 21  2  0
 15 22  1  0
 23 24  2  0
 24 25  1  0
 23 26  1  0
 25 27  1  0
 26 28  1  0
 27 29  1  0
 28 29  1  0
 14  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794885

   4-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,9,10,11-tetrahydro-7H-cyclohepta[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: 406.43

Molecular Weight (Monoisotopic): 406.1628

AlogP: 0.55

#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: 1.29

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 1.13

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