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(E)-11-[(Methoxycarbonylbutyl)oxyimino]strychnine ID: ALA4061219
PubChem CID: 137637510
Max Phase: Preclinical
Molecular Formula: C27H31N3O5
Molecular Weight: 477.56
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: COC(=O)CCCCO/N=C1/C(=O)N2c3ccccc3[C@@]34CCN5CC6=CCO[C@@H]1[C@@H]([C@H]23)[C@H]6C[C@H]54
Standard InChI: InChI=1S/C27H31N3O5/c1-33-21(31)8-4-5-12-35-28-23-24-22-17-14-20-27(10-11-29(20)15-16(17)9-13-34-24)18-6-2-3-7-19(18)30(25(22)27)26(23)32/h2-3,6-7,9,17,20,22,24-25H,4-5,8,10-15H2,1H3/b28-23+/t17-,20-,22-,24+,25-,27+/m0/s1
Standard InChI Key: LGGNLAFJHVCRSF-JMXFTUJVSA-N
Molfile:
RDKit 2D
40 46 0 0 0 0 0 0 0 0999 V2000
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13.1959 -12.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.1503 -10.8995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.4553 -11.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.8740 -11.2908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.8945 -12.1126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.6493 -11.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.2721 -10.8117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.7758 -10.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.9612 -10.2622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.1456 -11.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.6823 -12.3436 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
15.1565 -13.0696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.0209 -13.0410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.4263 -12.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.9551 -11.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.9658 -11.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.2394 -12.3239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
17.0413 -10.3759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.7124 -9.3564 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
16.5130 -9.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.7182 -10.5946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.0738 -10.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.4412 -9.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.8101 -13.8098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.5473 -12.3734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
15.3657 -10.9660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
16.9753 -11.2178 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
16.7400 -11.7750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
16.8267 -13.0297 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
16.4440 -13.7401 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
17.2610 -13.7232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
17.6841 -14.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.5011 -14.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.9242 -15.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.7412 -15.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.1644 -15.7869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.9814 -15.7700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
19.7704 -16.5029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
21.4045 -16.4692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 6 1 0
5 3 1 0
3 4 2 0
4 1 1 0
5 6 2 0
6 12 1 0
7 5 1 0
7 11 1 0
7 10 1 0
11 16 1 0
16 8 1 0
8 9 1 0
9 10 1 0
11 12 1 0
12 13 1 0
13 14 1 0
14 15 1 0
15 16 1 0
15 18 1 0
18 17 1 0
8 19 1 0
10 20 1 0
20 21 1 0
21 19 1 0
19 22 2 0
22 17 1 0
7 23 1 1
23 24 1 0
24 20 1 0
13 25 2 0
11 26 1 1
10 27 1 6
8 28 1 6
16 29 1 6
15 30 1 6
14 31 2 0
31 32 1 0
32 33 1 0
33 34 1 0
34 35 1 0
35 36 1 0
36 37 1 0
37 38 1 0
37 39 2 0
38 40 1 0
M END Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: 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: 477.56Molecular Weight (Monoisotopic): 477.2264AlogP: 2.42#Rotatable Bonds: 6Polar Surface Area: 80.67Molecular Species: BASEHBA: 7HBD: ┄#RO5 Violations: ┄HBA (Lipinski): 8HBD (Lipinski): ┄#RO5 Violations (Lipinski): ┄CX Acidic pKa: ┄CX Basic pKa: 9.30CX LogP: 2.11CX LogD: 0.22Aromatic Rings: 1Heavy Atoms: 35QED Weighted: 0.27Np Likeness Score: 1.90
References 1. Mohsen AM, Mandour YM, Sarukhanyan E, Breitinger U, Villmann C, Banoub MM, Breitinger HG, Dandekar T, Holzgrabe U, Sotriffer C, Jensen AA, Zlotos DP.. (2016) Oxime Ethers of (E)-11-Isonitrosostrychnine as Highly Potent Glycine Receptor Antagonists., 79 (12): [PMID:27966945 ] [10.1021/acs.jnatprod.6b00479 ]