Narcissidine

ID: ALA4552547

PubChem CID: 443686

Max Phase: Preclinical

Molecular Formula: C18H23NO5

Molecular Weight: 333.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)[C@@H]1[C@H](O)[C@@H](OC)[C@H](O)C3=CCN(C2)[C@H]31

Standard InChI:  InChI=1S/C18H23NO5/c1-22-12-6-9-8-19-5-4-10-15(19)14(11(9)7-13(12)23-2)17(21)18(24-3)16(10)20/h4,6-7,14-18,20-21H,5,8H2,1-3H3/t14-,15+,16+,17-,18-/m0/s1

Standard InChI Key:  OHZXJDOKMFHAFO-PNKHAZJDSA-N

Molfile:  

 
     RDKit          2D

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   13.5043   -6.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9117   -7.6808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9117   -6.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5084   -7.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6216   -5.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1977   -5.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8027   -6.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2100   -8.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9117   -5.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.6876   -7.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1664   -7.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9117   -4.4203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9117   -6.0546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3967   -8.0922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3989   -6.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4018   -5.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6897   -7.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2040   -4.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3328   -5.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6  2  1  0
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  8 17  1  6
 11 18  1  1
  1 19  1  1
  4 20  1  6
  5  7  1  0
 15 16  1  0
  6 10  1  0
 14 13  1  0
 13 21  1  0
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  7 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4552547

   Narcissidine

Molecule Features

Natural Product: Yes

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: 333.38

Molecular Weight (Monoisotopic): 333.1576

AlogP: 0.66

#Rotatable Bonds: 3

Polar Surface Area: 71.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.27

CX Basic pKa: 7.97

CX LogP: -0.05

CX LogD: -0.72

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 1.97

References

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

Source

Source(1):

• Scientific Literature