16-hydroxyhuperzine A

ID: ALA4786589

PubChem CID: 101518234

Max Phase: Preclinical

Molecular Formula: C15H18N2O2

Molecular Weight: 258.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(CO)C[C@]1(N)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C15H18N2O2/c1-2-11-10-5-9(8-18)7-15(11,16)12-3-4-14(19)17-13(12)6-10/h2-5,10,18H,6-8,16H2,1H3,(H,17,19)/b11-2+/t10-,15+/m0/s1

Standard InChI Key:  SDJTYVJCTXDMTK-DEOGUITISA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    5.9787  -13.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8684  -13.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8582  -12.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5150  -14.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5034  -13.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5360  -12.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5665  -13.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913  -12.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365  -13.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2403  -12.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7510  -12.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0569  -12.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2511  -13.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972  -14.2814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2279  -14.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513  -12.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366  -11.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4141  -15.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6890  -13.4963    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115  -10.6933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7  2  1  0
  8 12  2  0
  9  5  1  0
 10 13  1  0
 11  1  1  0
 12 11  1  0
 13  7  2  0
  1 14  1  1
 15  4  2  0
 16 10  2  0
 12 17  1  0
 18 15  1  0
  5 19  1  6
  8  5  1  0
  9  3  1  0
 10  6  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4786589

   (1R,9R,13E)-1-amino-13-ethylidene-11-(hydroxymethyl)-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 258.32

Molecular Weight (Monoisotopic): 258.1368

AlogP: 0.97

#Rotatable Bonds: 1

Polar Surface Area: 79.11

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.10

CX Basic pKa: 8.79

CX LogP: -0.66

CX LogD: -2.07

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.66

Np Likeness Score: 2.25

References

1. Zhu X,Xia D,Zhou Z,Xie S,Shi Z,Chen G,Wang L,Pan K.  (2020)  Lycosquarrines A-R, Lycopodium Alkaloids from Phlegmariurus squarrosus.,  83  (10): [PMID:32941036] [10.1021/acs.jnatprod.9b00815]

Source

Source(1):

• Scientific Literature