Anciscochine 6-O-beta-D-glucopyranoside

ID: ALA3827667

PubChem CID: 127044354

Max Phase: Preclinical

Molecular Formula: C18H23NO8

Molecular Weight: 381.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc2cc(CO)nc(C)c12

Standard InChI:  InChI=1S/C18H23NO8/c1-8-14-9(3-10(6-20)19-8)4-11(5-12(14)25-2)26-18-17(24)16(23)15(22)13(7-21)27-18/h3-5,13,15-18,20-24H,6-7H2,1-2H3/t13-,15-,16+,17-,18-/m1/s1

Standard InChI Key:  PSSBZWSRNFVSRY-SOVHRIKKSA-N

Molfile:  

     RDKit          2D

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    3.8942   -1.4964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4987   -2.6896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8323   -1.3315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8230    1.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877    0.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4338    3.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946   -1.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858    0.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4842    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4759    3.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396    3.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928    2.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091   -1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -2.7019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
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  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
  7  1  1  6
  8  2  1  1
  9  3  1  6
 10  4  1  1
 17 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 18  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
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 22 23  1  0
 23 24  1  0
 13 25  1  0
 15 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3827667

   ---

Molecule Features

Natural Product: No

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: 381.38

Molecular Weight (Monoisotopic): 381.1424

AlogP: -0.78

#Rotatable Bonds: 5

Polar Surface Area: 141.73

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 6.86

CX LogP: -1.54

CX LogD: -1.65

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: 1.62

References

1. Lien le Q, Linh TM, Giang VH, Mai NC, Nhiem NX, Tai BH, Cuc NT, Anh Hle T, Ban NK, Minh CV, Kiem PV..  (2016)  New naphthalene derivatives and isoquinoline alkaloids from Ancistrocladus cochinchinensis with their anti-proliferative activity on human cancer cells.,  26  (16): [PMID:27423477] [10.1016/j.bmcl.2016.07.014]

Source

Source(1):

• Scientific Literature