Dihydrocatalpol

ID: ALA471185

Cas Number: 6736-86-3

PubChem CID: 5705531

Max Phase: Preclinical

Molecular Formula: C15H24O10

Molecular Weight: 364.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dihydrocatalpol | Dihydrocatalpol|6736-86-3|beta-D-Glucopyranoside, (1aS,1bS,2S,6R,6aS,6bS)-octahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl|3,4-Dihydrocatalpol|CHEMBL471185|DTXSID001104596|HY-N9977|AKOS004901988|FS-7348|CS-0227093|E89020|(2S,3R,4S,5S,6R)-2-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]decan-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OCC[C@H]3[C@H](O)[C@@H]4O[C@]4(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H24O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h5-14,16-21H,1-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/m1/s1

Standard InChI Key:  NYCXYIWXBJWWIL-PZYDOOQISA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.5603    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483    0.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483    1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603    1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569    1.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765    2.2042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765   -0.2708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569    0.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447    0.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8754    0.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7820   -0.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2640    1.3792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    2.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603   -0.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5782   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5782   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338   -0.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500   -0.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597   -2.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921   -2.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338   -3.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -1.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
 13 14  1  0
  6  7  1  0
 11 15  1  6
  7 11  1  0
  7 16  1  1
 10  5  1  0
  1 17  1  1
  1  2  1  0
 17 18  1  0
 18 19  1  0
  6  8  1  1
  2  3  1  0
  5  9  1  1
 11 10  1  0
 12 11  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 10 12  1  0
 18 24  1  1
  3  4  1  0
 19 25  1  1
  5  6  1  0
 21 26  1  1
 22 27  1  6
  6  4  1  0
 20 28  1  6
 10 13  1  6
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA471185

   DIHYDROCATALPOL

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: 364.35

Molecular Weight (Monoisotopic): 364.1369

AlogP: -3.71

#Rotatable Bonds: 4

Polar Surface Area: 161.60

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.19

CX Basic pKa: ┄

CX LogP: -3.44

CX LogD: -3.44

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.27

Np Likeness Score: 2.94

References

1. Pungitore CR, Ayub MJ, García M, Borkowski EJ, Sosa ME, Ciuffo G, Giordano OS, Tonn CE..  (2004)  Iridoids as allelochemicals and DNA polymerase inhibitors.,  67  (3): [PMID:15043410] [10.1021/np030238b]

Source

Source(1):

• Scientific Literature