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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:  

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M  END

Alternative Forms

  1. Parent:

    ALA1651099

    ALSTOLUCINE A

Associated Targets(Human)

ABCC10 Tbio Multidrug resistance-associated protein 7 (31 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 412.49Molecular Weight (Monoisotopic): 412.1998AlogP: 3.06#Rotatable Bonds: 4
Polar 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: -0.27
Aromatic 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]

Source