Acetic acid 2-acetoxy-1-(3,4-dihydroxy-5-oxo-2,5-dihydro-furan-2-yl)-ethyl ester

Names and Identifiers

Canonical SMILES: CC(=O)OCC(OC(C)=O)C1OC(O)=C(O)C1=O

Standard InChI: InChI=1S/C10H12O8/c1-4(11)16-3-6(17-5(2)12)9-7(13)8(14)10(15)18-9/h6,9,14-15H,3H2,1-2H3

Standard InChI Key: PCEFFIBBQITJMP-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    7.6917   -7.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -6.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -6.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542   -6.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -5.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -6.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -7.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1042   -8.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -8.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -6.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -6.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1667   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -7.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  4  1  0
  6  3  1  0
  7  6  1  0
  8  7  1  0
  9  4  1  0
 10 14  1  0
 11  6  1  0
 12  1  1  0
 13  2  2  0
 14 11  1  0
 15  8  2  0
 16 10  2  0
 17  8  1  0
 18 10  1  0
  5  3  1  0
M  END

Alternative Forms

Parent:

ALA45567
[2-acetyloxy-2-(3,4-dihydroxy-5-oxo-2H-furan-2-yl)ethyl] acetate

Associated Targets(Human)

AMY2A Tclin Pancreatic alpha-amylase (74 Activities)

Discover Target: AMY2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ALP1 Alpha-amylase (16 Activities)

Discover Target: ALP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 260.20	Molecular Weight (Monoisotopic): 260.0532	AlogP: -0.27	#Rotatable Bonds: 4
Polar Surface Area: 119.36	Molecular Species: ACID	HBA: 8	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 8	HBD (Lipinski): 2	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 4.79	CX Basic pKa: ┄	CX LogP: -0.38	CX LogD: -2.70
Aromatic Rings: ┄	Heavy Atoms: 18	QED Weighted: 0.66	Np Likeness Score: 1.32

References

1. Abell AD, Ratcliffe MJ, Gerrard J.. (1998) Ascorbic acid-based inhibitors of alpha-amylases., 8 (13): [PMID:9873419] [10.1016/s0960-894x(98)00298-4]
2. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J.. (2015) From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors., 23 (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]

Source

Source(1):

Scientific Literature