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alstolucine A ID: ALA1651099
PubChem CID: 50899956
Max Phase: Preclinical
Molecular Formula: C23H28N2O5
Molecular Weight: 412.49
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Synonyms: Alstolucine A | CHEBI:70492|Alstolucine A|(-)-Alstolucine A, (rel)-|CHEMBL1651099|Q27138827
Canonical SMILES: CCOC(=O)O[C@H](C)[C@H]1CN2CC[C@]34C(=C(C(=O)OC)[C@H]1C[C@H]23)Nc1ccccc14
Standard InChI: InChI=1S/C23H28N2O5/c1-4-29-22(27)30-13(2)15-12-25-10-9-23-16-7-5-6-8-17(16)24-20(23)19(21(26)28-3)14(15)11-18(23)25/h5-8,13-15,18,24H,4,9-12H2,1-3H3/t13-,14+,15-,18+,23-/m1/s1
Standard InChI Key: BPXHFWZHURFHEN-KBHVJUHDSA-N
Molfile:
RDKit 2D
33 37 0 0 0 0 0 0 0 0999 V2000
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-5.4576 1.0550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.8909 0.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4212 2.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.8529 1.4433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.0884 0.6519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4085 0.1833 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.7535 0.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9431 0.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4008 1.1544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6748 1.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0274 1.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4910 2.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.9283 2.7994 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-3.7351 2.6018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.7962 1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2812 1.2988 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-0.8200 1.7442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9949 0.4454 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.0395 2.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0223 1.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.1974 0.7419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5560 2.1245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.3538 1.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9320 2.5046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.5733 1.1228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.7299 2.2975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3082 2.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6720 -0.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2104 -0.8747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.8622 -0.4049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.5911 -1.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4121 1.0324 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
15 16 1 0
12 16 1 1
12 5 1 0
13 17 1 6
12 8 1 0
18 10 1 0
1 2 2 0
10 19 1 6
5 4 2 0
18 20 1 0
14 20 1 0
4 1 1 0
21 18 1 0
5 6 1 0
21 22 1 6
8 9 2 0
21 23 1 0
10 9 1 0
23 24 1 0
10 11 1 0
24 25 1 0
11 13 1 0
24 26 2 0
12 13 1 0
25 27 1 0
27 28 1 0
2 3 1 0
3 6 2 0
9 29 1 0
6 7 1 0
29 30 2 0
7 8 1 0
29 31 1 0
13 14 1 0
31 32 1 0
14 15 1 0
18 33 1 1
M END Associated Targets(Human) Molecule Features Natural Product: YesOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 412.49Molecular Weight (Monoisotopic): 412.1998AlogP: 3.06#Rotatable Bonds: 4Polar Surface Area: 77.10Molecular Species: BASEHBA: 7HBD: 1#RO5 Violations: ┄HBA (Lipinski): 7HBD (Lipinski): 1#RO5 Violations (Lipinski): ┄CX Acidic pKa: 13.98CX Basic pKa: 9.97CX LogP: 2.25CX LogD: -0.27Aromatic Rings: 1Heavy Atoms: 30QED Weighted: 0.76Np Likeness Score: 1.56
References 1. Tan SJ, Low YY, Choo YM, Abdullah Z, Etoh T, Hayashi M, Komiyama K, Kam TS.. (2010) Strychnan and secoangustilobine A type alkaloids from Alstonia spatulata. Revision of the C-20 configuration of scholaricine., 73 (11): [PMID:21043460 ] [10.1021/np100552b ] 2. Teijaro CN, Munagala S, Zhao S, Sirasani G, Kokkonda P, Malofeeva EV, Hopper-Borge E, Andrade RB.. (2014) Synthesis and biological evaluation of pentacyclic strychnos alkaloids as selective modulators of the ABCC10 (MRP7) efflux pump., 57 (24): [PMID:25419978 ] [10.1021/jm501189p ]