Montanine

ID: ALA1221863

Cas Number: 642-52-4

PubChem CID: 11087935

Max Phase: Preclinical

Molecular Formula: C17H19NO4

Molecular Weight: 301.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Montanine | Montanine|642-52-4|(-)-Montanine|Compound NP-016462|SCHEMBL812255|CHEMBL1221863|DTXSID801107687|BDBM50190649|AKOS040738613|(1S,13S,15S,16S)-16-methoxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.013,18]nonadeca-2,4(8),9,17-tetraen-15-ol|(6R,6aS,8S,9S,11S)-5,6a,7,8,9,11-Hexahydro-9-methoxy-6,11-methano-6H-benzo[b]-1,3-benzodioxolo[5,6-e]azepin-8-ol

Canonical SMILES:  CO[C@H]1C=C2[C@H]3CN(Cc4cc5c(cc43)OCO5)[C@H]2C[C@@H]1O

Standard InChI:  InChI=1S/C17H19NO4/c1-20-15-4-11-12-7-18(13(11)5-14(15)19)6-9-2-16-17(3-10(9)12)22-8-21-16/h2-4,12-15,19H,5-8H2,1H3/t12-,13-,14-,15-/m0/s1

Standard InChI Key:  MKYLOMHWHWEFCT-AJNGGQMLSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   11.7597  -27.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7579  -25.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0235  -26.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0202  -25.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2083  -25.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7093  -26.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2138  -26.8998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9628  -26.9416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1534  -27.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5052  -26.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4988  -25.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1156  -25.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9118  -25.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2965  -26.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1007  -26.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5261  -25.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1464  -24.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3312  -24.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3592  -25.5028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5652  -24.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4080  -24.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3166  -26.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9223  -24.4645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7484  -26.8613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1 10  2  0
 11  2  2  0
  2  4  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  8 14  1  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 10  1  0
 13 14  1  0
 13 18  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  1
 17 20  1  6
 20 21  1  0
 12 22  1  0
  8 22  1  0
 12 23  1  6
 14 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1221863

   MONTANINE

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

Calculated Properties

Molecular Weight: 301.34

Molecular Weight (Monoisotopic): 301.1314

AlogP: 1.40

#Rotatable Bonds: 1

Polar Surface Area: 51.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.02

CX LogP: 0.69

CX LogD: -0.02

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: 2.12

References

1. McNulty J, Nair JJ, Little JR, Brennan JD, Bastida J..  (2010)  Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids.,  20  (17): [PMID:20655219] [10.1016/j.bmcl.2010.06.130]

2. Ortiz JE, Pigni NB, Andujar SA, Roitman G, Suvire FD, Enriz RD, Tapia A, Bastida J, Feresin GE..  (2016)  Alkaloids from Hippeastrum argentinum and Their Cholinesterase-Inhibitory Activities: An in Vitro and in Silico Study.,  79  (5): [PMID:27096334] [10.1021/acs.jnatprod.5b00785]

3. Nair JJ, Wilhelm A, Bonnet SL, van Staden J..  (2017)  Antibacterial constituents of the plant family Amaryllidaceae.,  27  (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052]

4. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

5. Maafi N, Pidaný F, Maříková J, Korábečný J, Hulcová D, Kučera T, Schmidt M, Shammari LA, Špulák M, Carmen Catapano M, Mecava M, Prchal L, Kuneš J, Janoušek J, Kohelová E, Jenčo J, Nováková L, Cahlíková L..  (2021)  Derivatives of montanine-type alkaloids and their implication for the treatment of Alzheimer's disease: Synthesis, biological activity and in silico study.,  51  [PMID:34555506] [10.1016/j.bmcl.2021.128374]

Source

Source(1):

• Scientific Literature