Siringate-4-O-beta-D-glucopyranoside

ID: ALA5082798

Cas Number: 33228-65-8

PubChem CID: 10383888

Max Phase: Preclinical

Molecular Formula: C15H20O10

Molecular Weight: 360.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)O)cc(OC)c1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)/t9-,10-,11+,12-,15+/m1/s1

Standard InChI Key:  BLKMDORKRDACEI-OVKLUEDNSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    0.3586    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -0.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    0.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    2.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144    0.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144   -0.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -1.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.4140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  8  7  1  1
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
  8 13  1  0
 12 14  1  1
 14 15  1  0
 11 16  1  6
 10 17  1  1
  9 18  1  6
  1 19  1  0
 19 20  1  0
  5 21  1  0
 21 22  1  0
  3 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5082798

   Glucosyringic acid

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: 360.32

Molecular Weight (Monoisotopic): 360.1056

AlogP: -1.42

#Rotatable Bonds: 6

Polar Surface Area: 155.14

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: -1.26

CX LogD: -4.48

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: 1.57

References

1. Munsimbwe L, Suganuma K, Ishikawa Y, Choongo K, Kikuchi T, Shirakura I, Murata T..  (2022)  Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities.,  85  (1.0): [PMID:34965114] [10.1021/acs.jnatprod.1c00738]

Source

Source(1):

• Scientific Literature