Isonarciclasine

ID: ALA476486

PubChem CID: 5479394

Max Phase: Preclinical

Molecular Formula: C14H13NO7

Molecular Weight: 307.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isonarciclasine | Isonarciclasine|CHEMBL476486|(2S,3R,4S)-2,3,4,7-tetrahydroxy-2,3,4,5-tetrahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one|[1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 1,3,4,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S)-

Canonical SMILES:  O=c1[nH]c2c(c3cc4c(c(O)c13)OCO4)C[C@H](O)[C@@H](O)[C@H]2O

Standard InChI:  InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h2,6,10,12,16-19H,1,3H2,(H,15,20)/t6-,10+,12-/m0/s1

Standard InChI Key:  JIMDZZQKKBUKLO-QDWQASTRSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   15.9232  -19.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2113  -19.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2113  -18.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4224  -17.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9348  -18.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4223  -19.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9232  -17.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6357  -18.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6362  -19.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3478  -19.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0633  -19.0808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467  -17.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0635  -18.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7795  -17.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7848  -17.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0680  -16.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3458  -17.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0718  -15.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3471  -20.3169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9230  -20.3150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5013  -16.6101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4918  -18.2640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  7  8  2  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  9  1  0
 16 18  1  6
  3  7  1  0
 10 19  2  0
  2  1  1  0
  1 20  1  0
  1  9  2  0
 15 21  1  1
  2  3  2  0
 14 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA476486

   ISONARCICLASINE

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: 307.26

Molecular Weight (Monoisotopic): 307.0692

AlogP: -0.73

#Rotatable Bonds: ┄

Polar Surface Area: 132.24

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.38

CX Basic pKa: ┄

CX LogP: -0.93

CX LogD: -0.97

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.43

Np Likeness Score: 1.86

References

1. Gabrielsen B, Monath TP, Huggins JW, Kefauver DF, Pettit GR, Groszek G, Hollingshead M, Kirsi JJ, Shannon WM, Schubert EM..  (1992)  Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.,  55  (11): [PMID:1336040] [10.1021/np50089a003]

Source

Source(1):

• Scientific Literature