ID: ALA4299399

Max Phase: Preclinical

Molecular Formula: C25H43NO18

Molecular Weight: 645.61

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@H]2CO)[C@@H](O)[C@H](O)[C@H]1N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8-,9+,10-,11-,12+,13-,14+,15-,16+,17-,18+,19-,20-,21+,22-,23?,24-,25-/m0/s1

Standard InChI Key:  XUFXOAAUWZOOIT-ZJGALDLUSA-N

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

Properties

Molecular Weight: 645.61

Molecular Weight (Monoisotopic): 645.2480

AlogP: -8.56

#Rotatable Bonds: 9

Polar Surface Area: 321.17

Molecular Species: NEUTRAL

HBA: 19

HBD: 14

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.23

CX Basic pKa: 7.03

CX LogP: -7.61

CX LogD: -7.77

Aromatic Rings: 0

Heavy Atoms: 44

QED Weighted: 0.10

Np Likeness Score: 1.83

References

1. Imran S, Taha M, Ismail NH, Kashif SM, Rahim F, Jamil W, Hariono M, Yusuf M, Wahab H..  (2015)  Synthesis of novel flavone hydrazones: in-vitro evaluation of α-glucosidase inhibition, QSAR analysis and docking studies.,  105  [PMID:26491979] [10.1016/j.ejmech.2015.10.017]

2. Toh ZS, Wang H, Yip YM, Lu Y, Lim BJ, Zhang D, Huang D..  (2015)  Phenolic group on A-ring is key for dracoflavan B as a selective noncompetitive inhibitor of α-amylase.,  23  (24): [PMID:26631440] [10.1016/j.bmc.2015.11.008]

3. Taha M, Ismail NH, Imran S, Wadood A, Rahim F, Ali M, Rehman AU.  (2015)  Novel quinoline derivatives as potent in vitro -glucosidase inhibitors: in silico studies and SAR predictions,  6  (10): [10.1039/C5MD00280J]

4. Zhang LH, Feng BM, Zhao YQ, Sun Y, Liu B, Liu F, Chen G, Bai J, Hua HM, Wang HF, Pei YH..  (2016)  Polyketide butenolide, diphenyl ether, and benzophenone derivatives from the fungus Aspergillus flavipes PJ03-11.,  26  (2): [PMID:26706176] [10.1016/j.bmcl.2015.12.009]

5. Chen J, Wu Y, Zou J, Gao K..  (2016)  α-Glucosidase inhibition and antihyperglycemic activity of flavonoids from Ampelopsis grossedentata and the flavonoid derivatives.,  24  (7): [PMID:26922036] [10.1016/j.bmc.2016.02.018]

6. Islam MS, Barakat A, Al-Majid AM, Ghabbour HA, Rahman AF, Javaid K, Imad R, Yousuf S, Choudhary MI..  (2016)  A concise synthesis and evaluation of new malonamide derivatives as potential α-glucosidase inhibitors.,  24  (8): [PMID:26972921] [10.1016/j.bmc.2016.02.037]

7. Johnson OO, Zhao M, Gunn J, Santarsiero BD, Yin ZQ, Ayoola GA, Coker HA, Che CT..  (2016)  α-Glucosidase Inhibitory Prenylated Anthranols from Harungana madagascariensis.,  79  (1): [PMID:26727375] [10.1021/acs.jnatprod.5b00924]

8. Wang G, Wang J, He D, Li X, Li J, Peng Z..  (2016)  Synthesis and biological evaluation of novel 1,2,4-triazine derivatives bearing carbazole moiety as potent α-glucosidase inhibitors.,  26  (12): [PMID:27177827] [10.1016/j.bmcl.2016.04.071]

9. Tanabe G, Xie W, Balakishan G, Amer MF, Tsutsui N, Takemura H, Nakamura S, Akaki J, Ninomiya K, Morikawa T, Nakanishi I, Muraoka O..  (2016)  Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia'.,  24  (16): [PMID:27325449] [10.1016/j.bmc.2016.06.013]

10. Suresh L, Onkara P, Kumar PS, Pydisetty Y, Chandramouli GV..  (2016)  Ionic liquid-promoted multicomponent synthesis of fused tetrazolo[1,5-a]pyrimidines as α-glucosidase inhibitors.,  26  (16): [PMID:27406797] [10.1016/j.bmcl.2016.06.086]

Source

Source(1):

• Scientific Literature